INDEX

CH. NO. CHAPTER NAME PAGE NO.

11. NOMENCLATURE 2 - 63
12. GENERAL ORGANIC CHEMISTRY 64 - 162
13. ISOMERISM 163 - 212
14. HYDROCARBONS 213 - 236

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CHAPTER-11
NOMENCLATURE
Nomenclature means the “system of naming organic compounds based on certain
guidelines”.
In order to solve the problem of naming of organic compounds, an organization called
international chemical congress for the first time met at Geneva in 1892. They developed
a certain system called Geneva system. This system was modified as I.U.C. system in a
meeting of international Union of Chemistry held in Liege (Belgium) in 1930 and later on it
gave to another modified system known as IUPAC system which is a system adopted by
the International Union of Pure and Applied Chemistry. The latest IUPAC system is based
on the recommendations made in 1993.

Classification of organic Compounds

If we look at the vast multitude of organic compounds, two things will strike our mind. The
skeleton is either open or closed. Based on this, organic compounds are classified as
acyclic (open-chain) or cyclic (closed-chain)

Organic Compounds

Open chain or acyclic Closed chain or

or aliphatic comopund cyclic compounds

Alkanes Alkenes Alkynes Aliphatic compounds Homocylic Heterocyclic

with other functional group compounds compounds

Alicyclic Aromatic Alicyclic Aromatic

compound compounds

Benzenoid Aromatic Non-Benzenoid

Compounds Aromatic compound

1. Acyclic or open - chain compounds

These are the compound in which the carbon atoms are linked to each other in such a
manner that the molecule is having an open-chain structure. The chain of the carbon
atoms may be straight or branched. These compounds are also called as aliphatic
compounds.
Example :
Alkanes CH3 – CH2 – CH3 Propane
Alkenes CH3 – CH = CH2 Propene
Alkynes HC  CH Ethyne
Aliphatic compound with other
function group CH3 – CH2 – OH Ethanol

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2. Cyclic or closed - chain compounds

These are the compounds in which carbon atoms are linked to each other or to the
atoms of other element in a manner that a ring structure is formed. The compounds with
only one ring of atoms in the molecule are known as monocyclic but these with more
than one ring of atoms are termed as polycyclic.
These are further divided into two subgroups
(a) Homocyclic or carbocyclic, (b) Heterocyclic.

[a] Homocyclic or Carbocyclic

These are the compound which contain rings of three or more carbon atoms. The
homocyclic compounds may be alicyclic or aromatic depending on whether they resemble
aliphatic compounds or not.
(i) Alicyclic compounds :
Example :
CH2

H2C CH2
Cyclohexane Cyclopropane (monocyclic)
(ii) Aromatic compounds :
These compounds consist of at least one benzene ring, i.e.a six-membered carbocyclic
ring having alternate single and double bonds. Strictly speaking these are called benzenoid
aromatics.
Example :
Homocyclic benzenoid aromatic compounds
OH

Benzene Phenol Napthalene

Homocyclic Non-benzenoid aromatic compounds

[18] annulene

[b] Heterocyclic
Cyclic compounds contaning one or more heteroatoms (e.g. O, N, S etc.) in the ring are
called heterocyclic compounds. These are of two types
(i) Non aromatic heterocyclic compounds (alicyclic heterocyclic compounds) :
Heterocyclic compounds which resemble aliphatic compounds in their properties
are called alicyclic heterocyclic compounds. For examples,
Example : O
O
O O
Oxirane or Ethylene epoxide Tetrahydrofuran 1,4-Dioxan
(Epoxyethane)
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H
N
O
Pentahydropyran Azacyclopentane
(ii) Aromatic heterocyclic compounds : Heterocyclic compounds whihc resemble b
benzene and other aromatic compounds in most of their properties are called aromatic
heterocyclic compounds. For example,
Example :

N
O S N N H
Furan Thiophene Quinoline Pyridine Pyrrole

3. Type of carbon and Hydrogen atoms in Alkanes

The carbon atoms in an alkane molecule may be classified into four types as primary (1º),
secondary (2º), tertiary (3º) and quaternary (4º) as follows
(i) Primary Carbon
A carbon atom attached to one another (or no other) carbon atom is called a primary
carbon atom and is designated as 1º carbon
Example :
1º 1º 1º 1º
(i) CH3 – CH3 (ii) CH3 – CH2 – CH3
(ii) Secondary Carbon
A carbon atom attached to two other carbon atoms is called a secondary carbon atom
and is designated as 2º carbon
Example :
2º 2º 2º
(i) CH3 – CH2 – CH3 (ii) CH3 – CH2 – CH2 – CH3
(iii) Tertiary Carbon
A carbon atom attached to three other carbon atoms is called a tertiary carbon atom and
is designated as 3º carbon
Example :
CH3 CH3
(i) CH3 – CH – CH3 (ii) CH3 – CH – CH2 – CH3
3º 3º
(iv) Quaternary Carbon
A carbon atom attached to four other carbon atoms is called a quaternary carbon atom
and is designated as 4º carbon.
Example :
CH3 CH3
4º 4º
(i) CH3–C–CH3 (ii) CH3 – C – CH2 – CH3

CH3 CH2
The hydrogen atoms attached to 1º, 2º and 3º carbon atoms are called primary (1º)
secondary (2º) and tertiary (3º) hydrogen atom. It may be noted here that there is nothing
like quaternary hydrogen atom, since a quarternary carbon does not carry any hydrogen

4. Organic Compound and Functional Groups

Number of known organic compounds is much more than inorganic compounds but, it
has been possible to group them into classes or families based on their structural features.

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This has given organic chemistry a logical and systematic shape.

In these compouds, there are a number of atoms or groups which show constancy of
properties. Such groups are called functional groups. Examples of functional groups are:
4.1 [a] Alkanes
These are open-chain aliphatic compounds which have no functional groups. These are
represented by the general formula, C nH2n+2
where n = 1, 2, 3, ..........
The names of the alkanes for n = 1, 2, .........., 10 must be committed to memory since all
of organic nomenclature is related directly or indirectly to the name of alkane C nH2n+2
n = 1 means CH4 – Methane C11 Undec
n = 2 means C2H6 – Ethane C 12 Dodec
n = 3 means C3H8 – Propane C 13 Tridec
n = 4 means C4H10 – Butane C 14 Tetradec
n = 5 means C5H12 – Pentane C 15 Pentadec
n = 6 means C6H14 – Hexane C 16 Eicos
n = 7 means C7H16 – Heptane C 17 Triacont
n = 8 means C8H18 – Octane C 18 Tetracont
n = 9 means C9H22 – Nonane C 19 Tetracont
n = 10 means C10H22 – Decane C 20 Pentacont

[b] Alkyl Groups

When we remove a hydrogen from alkane, we get an alkyl group:
H
General formula CnH2n + 2  CnH2n+1
ane
Alkane   alkyl
 yl

ane H
Example :. Methane  methyl CH4  – CH3
 yl
ane H
Propane  propyl C3H8  – C3H7
 yl

SOME COMMON NAMES OF HYDROCARBON ALKYL GROUPS

(i) Primary Alkyl group

A compound having CH3CH2– group is called primary alkyl group.
Example : CH 3CH 2– CH 3CH 3
Primary alkyl Ethane

(ii) Iso Alkyl group

CH3
A compound having – CH – CH3 group is called iso alkyl group

Example : CH 3 – CH– CH3 – CH – CH2 – CH3 – CH – CH2 – CH2–

CH3 CH3 CH3
Iso propyl Iso butyl Isopentyl

Note: Iso alkyl group name can be used in IUPAC Nomenclature and its first letter 'I' is
consider for alphabetical seniority.
Example :.

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1 2 3 4 5 6
CH3 – CH – CH – CH3 – CH3 – CH3
CH3 CH – CH3
CH3
3-Isopropyl–2–methylhexane
(iii) Neo Alkyl group
CH
Compound having CH3 – C – CH2 – group is called neo alkyl group.
CH3
Example :
CH3 CH3
CH2 – C – CH2 – (Neopentyl) CH3 – C – CH3 (Neopentane)
CH2 CH3

CH3 CH3
CH3 – C – CH2 – CH3 (Neohexane) CH3 – C – CH2 – CH – CH3 (Isooctane)
CH3 CH3 CH3

Key Concept - 1

1. In which of the following tert. carbon is absent

(A) Iso octane (B) Triptane (C) Isopropyl amine (D) Isopentane

2. How many 1ºcarbon atom will be present in a simplest hydrocarbon having two 3º and
one
2º carbon atom?
(A) 3 (B) 4 (C) 5 (D) 6

3. How many secondary carbon atoms does methyl cyclopropane have?

(A) None (B) One (C) Two (D) Three

4. The molecular formula of compound A is (C6H14). The structure of isomer of compound A

which have two tertiary and remaining primary hydrogen is present :
CH3

(A) CH3 – C – CH2 – CH3 (B) CH3 – CH – CH2 – CH 2CH3

CH3 CH3

CH3 CH3
(C) CH3 – CH2– CH2 –CH2 – CH2CH3 (D) CH3 – CH – CHCH3
5. Which of the following is an example of secondary alcohol :

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(A) CH3 – CH – CH2 – CH3 (B) CH3 – CH2 – CH2 – CH2

OH OH
CH3

(C) CH3 – C – CH2 – CH3 (D) CH3OH

OH

6. How many 3º and 1º carbon atoms present in following molecules.

CH3 CH3

(A) CH3 – C – CH3 (B) CH3 – C – CH3

Cl OH
7. How many 3º carbon atoms present in following molecule
CH3
CH3

(A) (B)

8. How many 1º, 2º, 3º and 4º carbon atoms are present in following molecule.
CH3
CH3 – CH – C – CH2 – CH – CH3

CH3 CH3 CH2 – CH3

9. How many 1º, 2º , 3º and 4º carbon atoms are present in following molecule
CH3
CH3 – C – CH2 – CH – CH3
CH3 CH3
10. The molecular formula of compound A is (C8H18). Write the structure of isomer of compound
A which has only primary hydrogen.
11. Write the structure A(C6H12) that has only secondary hydrogens.
12. Write the structure A(C6H14) that has 4 PC–H and 2 tC–H .

4.2 [a] Alkenes

Alkenes are open chain hydrocarbons and having carbon-carbon double bonds, C = C.
They have the general formula CnH2n where n = 2, 3, 4 ... etc. and are also called alkylenes
or olefins. The first three members are commonly named by their common names:
CH3

CH2 = CH2 CH3 – CH = CH2 CH3 – CH – CH = CH2 CH3 – C = CH2

ethylene propylene butylene isobutylene
4.2 [b] Alkenyl Groups
Like alkyl groups (alkane –H), there are three commonly encountered groups which are
given common names.

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remove
Example :. CH2 = CH2   CH2 = CH–
end H
vinyl group
remove H CH2 = CH – CH2–
from C3
1 2 3
Allyl (2-propenyl)
CH2 = CH – CH3
remove H
CH2 = C –
from C2

CH3
Isopropenyl group
4.3 Alkynes
Unsaturated aliphatic hydrocarbons containing a carbon-carbon triple bond are called
alkynes. In the common system, they are called acetylenes after the name of the first
member of this family. i.e. acetylene
General formula CnH2n – 2 where n = 2, 3, 4 ..... etc.
Common Names Acetylene and its alkyl derivatives.
IUPAC names Alkane – ane + yne = Alkyne
The position of the triple bond on the parent chain is designated by lowest possible arabic
numerals
The common IUPAC names of a few simple alkynes are given below.
n = 2  CH  CH Acetylene
n = 3  CH3 – C  CH Methyl acetylene
n = 4  CH3 – CH2 – C  CH Ethylacetylene

CH3
n = 6  Methyl isopropyl acetylene
CH3

4.4 Functional group and residue

The characteristic group of atom which decided the physical and chemical properties of
an organic molecules is called functional group.
Functional group is that portion of molecule which is highly reactive and takes part in
chemical reactions. Rest of the molecule is called residue.
Example :. CH3CH2CH2CH2 – COOH
Residue Functional
group
4.5 Functional groups

1. R – COOH Carboxylic acid 2. R – SO3H Sulphonic acid

3. R– C – O – C – R Anhydride 4. R – COOR Ester

O O
5. R– C –X Acid halide 6. R – C –NH2 Amide

O O
7. R–CN Alkane nitrile 8. R– C –H Aldehyde

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9. R– C –R Ketone 10. R – OH Alcohol

O
11. R – SH Thiol 12. R – NH2 Amine

EXAMPLES OF COMPOUND CONTAING

DIFFERENT FUNCTIONAL GROUPS
(A) – COOH group
(i) HCOOH Formic acid
(ii) CH 3COOH Acetic acid
(iii) CH3–CH2–COOH Propionic acid

(B) – SO3 H group

(i) CH 3SO 3H Methane sulphonic acid
(ii) CH 3CH 2SO 3H Ethane sulphonic acid
(iii) CH3 –CH2 – CH2 – SO3H Propane sulphonic acid

(C) – C – O – group

O O O
(i) CH3– C –O– C –CH3 Acetic anhydride

O O
(ii) CH3–CH2– C –O– C – CH2–CH3 Propionic anhydride
O O
(iii) CH3–CH2–CH2– C –O– C –CH2–CH2–CH3 Butanoic anhydride

(D) – C – O – R' group

O
O
(i) H – C – OCH3 Methyl formate
O
(ii) H – C – O – C2H5 Ethyl formate
O
(iii) CH3 – C – O – C2H5 Ethyl acetate

(E) – C – X group

O
(i) H – C – Cl Formyl chloride

O
(ii) CH3 – C – Br Acetyl bromide

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(iii) CH3 – CH2 – CH2 – C – Cl n-Butyryl chloride

O
(F) – C – NH2 group

O O
(i) H– C –NH2 Formamide
O
(ii) CH3– C –NH2 Acetamide
O
(iii) CH3–CH2– C –NH2 Propanamide
O
C–NH2
(iv) Benzamide

(G) – C – H group

O O
(i) H– C –H Formaldehyde
(ii) CH3 – CHO Acetaldehyde
(iii) CH3 –CH2 – CH2 – CHO n-Butyraldehyde
(H) – C  N group
(i) CH3 – CN Methyl cyanide or acetonitrile
(ii) CH3 – CH2 – CN Ethyl cyanide or propionitrile
(iii) CH3 – CH2 – CH2 – CN n-Prop yl cyanide o r n-
Butyronitrile
(I) – C – R' group

O
(i) CH3 – C – CH3 Dimethyl ketone or acetone

O
(ii) CH3 – C – CH2 – CH3 Ethylmethyl ketone

O
(iii) CH3 – C – CH2 – CH2 – CH3 Methyl n-propyl ketone

O
(J) – OH group
(i) CH3 – OH Methyl alcohol
(ii) CH3 – CH – CH3 Isopropyl alcohol

OH
(iii) CH3 – CH2 – CH2 – OH n-Propylalcohol
(K) – SH group
(i) CH3 – SH Methane thiol
(ii) CH3 – CH2 – SH Ethane thiol
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(iii) CH3 – CH2 – CH2 – SH Propane thiol
(L) – NH2 group
(i) CH3 – NH2 Methylamine or Aminomethane
(ii) CH3 – CH2 – NH – CH3 Ethyl methyl amine or
N-methylaminoethane
(iii) (CH3)3N Trimethylamine or
N, N-Dimethyl aminomethane

5. Nomenclature of Organic Compounds

IUPAC system of nomenclature of Aliphatic compounds

According to IUPAC system, the name of an organic compound consists of three parts
(i) Word root (ii) Suffix (iii) Prefix
(i) Word root
Word root denotes the number of carbon atoms present in the principal chain which is the
longest possible chain of carbon atoms.
According to chain length word root name up C12 are given below.
Chain Length Word root Chain Length Word Root
C1 Meth C7 Hept (a)
C2 Eth C8 Oct(a)
C3 Prop C9 Non(a)
C4 But(a) C 10 Dec(a)
C5 Pent(a) C11 Undec (a)
C6 Hex(a) C 12 Dodec(a)

Note. Extra ‘a’ given in parenthesis is used only if the primary suffix (discussed later) to
be added to the word root starts with a consonant.
Consonant – di, tri, tetra etc are not started with vowel, then extra ‘a’ has been added to
the word root.

(ii) Suffix
Suffixes are of two types. Primary and secondary suffixes.
(a) Primary suffix : A primary suffix indicates the type of linkage in the carbon atoms.
If the carbon atoms are linked by single covalent bonds, the primary suffix is ‘ane’.
If these are linked by double and triple bonds, the primary suffixes ‘ene’ and ‘yne’
are respectively used to represent them. Thus,
ane : primary suffix for C – C bond
ene : primary suffix for C = C bond
yne : primary suffix for C C bond
If the parent chain of carbon atoms contains more than one double or triple bonds, numerical
prefixes like di (for two), tri (for three) tetra (for four) etc. are added to primary suffix.
Example :.
Hydrocarbon Word root Primary suffix IUPAC Name
CH3–CH2 – CH2 – CH3 But ane Butane
CH2 = CH – CH = CH2 Buta* diene Butadiene
CH3 –CCH Prop yne Propyne

(b) Secondary suffix : A secondary suffix is used to represent the functional group if
present in organic molecule and is attached to the primary suffix while writing its
IUPAC name. Secondary suffixes of some of the functional groups are listed –

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Functional group Symbol Suffix Prefix

Carboxylic –COOH –oic acid carboxy
Sulphonic –SO3H sulponicacid sulpho

Ester Alkyl - Alkanonate alkyl carboxylate or

alkoxy carbonyl

Functional group Symbol Suffix Prefix

Acid halide - oylhalide Halo formyl

Acid Amide amide carbamoyl

Aldehyde –al Formyl/ Aldo

cynide –CN –nitrile Cyano

isocynide NC –isocynide Isocyano
ketone >C=O – one keto, oxo
hydroxy –OH –ol hydroxy
Thioalcohol – SH –Thiol mercapto
Amine –NH2 –Amine amino

Secondary amine N-Alkyl-amine N-alkyl-amine

Tertiaryamine N-alkyl-N-alkyl-amine N-alkyl-N-alkyl-amine

O
+
Nitro –N nitrite nitro
O-

Groups given below does not have any Suffix

Ether – OR ................................ alkoxy
Epoxide –O– ................................ epoxy
Azo –N=N– ................................ azo
Nitroso – NO ................................ nitroso
Halogen – X (F, Cl, Br, I)................................halo

While adding a secondary suffix to the primary suffix, the terminal ‘e’ of the primary suffix
(ane, ene, or yne) is dropped if the secondary suffix begins with ‘a’, ‘i’ ‘o’ ‘u’ or ‘y’. In case,
it begins with consonant, then the terminal ‘e’ of the primary suffix is retained.
Example
Organic compounds Word root Primary suffix Secondary suffix I U P A C
Name
CH3CH 2OH Eth an(e)* ol Ethanol

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CH 3CH 2CHO prop ane(e)* al Propanal
CH3CH2CH2NH 2 prop ane(e)* amine Propanamine
CH3CH2CN Prop ane nitrile Propanenitrile

(iii) Prefix
Prefix is a part of IUPAC name which appear before the word root. Prefixes are of two
types.
(a) Primary prefix : A primary prefix “cyclo” is used in order to differentiate a cyclic
compound from an acyclic compound.
Example:
H2C CH2

H2C CH2
Cyclobutane

Propane and butane are the IUPAC names of acyclic compounds while cyclopropane and
cyclobutane are for cyclic compounds.

(b) Secondary prefix : In the IUPAC system of nomenclature, certain characteristic

groups are not considered as or secondary suffixes. These are regarded as
substituents and are denoted by secondary prefixes.
The secondary prefixes of a few substituents are given :
Substituent Group Secondary prefix Substituent group Secondary prefix
–F Fluoro – NO 2 Nitro
– Cl Chloro – CH3 Methyl
– Br Bromo – C 2H 5 Ethyl
–I Iodo – OCH3 Methoxy
– NO Nitroso – OC2H5 Ethoxy

Besides these, some other functional groups are also treated as substituents in case of
poly functional organic compounds. These are listed as :

6. General rules for naming long chain aliphatic compounds

Many organic compounds contain long chains which may include substituents, multiple
bonds and functional groups. The IUPAC names of such compounds are based on certain
general rules.

Rules for IUPAC nomenclature of saturated Branched chain Hydrocarbons (Alkanes)

The nomenclature of branched chain alkanes is based on the following rules :
In writing the IUPAC name of an aliphatic compounds the following sequence is used
Secondary prefix + primary prefix + word root + primary suffix + secondary suffix

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1. Longest chain rule : Select the longest continuous chain of carbon atoms in a given
molecule of
alkane which need not be straight. It is known
as parent chain or principal chain. All other
carbon atoms which are not covered into the
parent chain constitute branched chains or
side chains or substituents.
If two chains of equal lengths are possible, then the one with more number of side chains
(or substituents) represents the parent chain. For example,

2. Lowest number rule : For molecules with only one substituent, number the carbon atoms
as 1, 2, 3, 4 ....... etc. in the parent chain starting from one end in such a way that the
carbon atom carrying the substituent gets the lowest number.

The number which indicates the position of the substituent (or side chain) in the parent
chain is called its position number or locant.
The name of the substituents is separated from its locant by hyphen (-) and the final
name of the alkane is always written as one word i.e. 3-methylheptane. In case, same
alkyl group occurs more than once at different positions in the parent chain, the positional
number of each alkyl group is separated by commas and suitable prefixes like di (for two),
tri (for three) tetra (for four) etc. are attached to the name of the alkyl groups.

3. Lowest set of locants rule : In case, there are two or more substituents, then the parent
or principal chain is numbered from the end which gives the lowest set of locants. The
rule is known as the lowest set of locant rules and according to it, when two or more
different sets of locants containing the same number of terms are possible, then that set
of locants is the lowest, which when compared term by term with other sets, each in
order of increasing magnitude has the lowest term at the first point of difference.
CH3 CH3

CH3 – C – CH2 – CH – CH3

CH3
2, (4) , 4
(wrong)

* Earlier lowest sum rule was followed and according to it the numbering of the chain was
done in such a way that the total sum of the locants must be lowest but actual emphasis
must be laid to have the lowest locant for the first selected term.

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Example:

Set of locant - (2, 7, 8) Sum = 2 + 7 + 8 = 17

CH3 CH3 CH3

H3C – CH – CH2 – CH2 – CH2 – CH2 – CH – CH – CH2 – CH3
10 9 8 7 6 5 4 3 2 1
Set of locant - (3, 4, 9) Sum = 3 + 4 + 9 = 16

4. Alphabetical order for the side chain (or substituents) : When two or more different
alkyl groups (side chains or substituents) are present on the parent chain. Such groups
prefixed by their locants (or positional numbers) are arranged in alphabetical order
irrespective of their positional number, before the name of the parent alkane. For example,

It may be remembered that the prefixes di, tri, tetra are not considered in case the same
alkyl group occurs more than on the parent chain at different positions while arranging
them in an alphabetical order.
CH2 –CH3
Example :
5 4 3 2 1
CH3 – CH2 – C – – CH – CH3
CH3 CH3
3-Ethyl-2,3-dimethylpentane
5. Naming the different substituents at equivalent positions :
If two different substituents are present at equivalent positions from the two ends in the
parent chain, then the numbering of the chain is done in such a way that the substituent
which comes first in the alphabetical order gets the lower number. For example
Example :

6. Naming the complex substituents or alkyl groups :

(a) An alkyl group is said to be complex in case one or more carbon atoms in it are further
substituted i.e., it is a substituted substituent (or alkyl group). It is named as a substituted
alkyl group by numbering from the carbon atom of this group attached to the parent chain
as “1”. The name of the complex substituent is generally enclosed in brackets in order to
avoid any confusion with either numbering the parent chain or naming the other substituents
attached to the chain.

Example :

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(b) It may be noted that while deciding the alphabetical order of the various substituents, the
name of the complex substituent is considered to begin with the first letter of its complete
name.

Example :

(c) When the names of the complex substituents are composed of identical words, the priority
is decided by comparing the locant at the first cited point within the complex substituents.
This means that the complex substituent gets lower priority which has the lowest locant.
Example :

5-(1-methylpropyl)–6–(2-methyl propyl) decane

In this case, 1-methylpropyl gets priority over 2-methylpropyl since the locant for the methyl
substituent in the first case is less.

Key Concept - 2
1. The IUPAC name of Br2CH – CH – CH – CBr3

C2H5 C2H5
(A) 3-(Dibromomethyl)-4-(tribromomethyl) hexane
(B) 1,1,1,4,4-Pentabromo-2,3-diethylbutane
(C) 4-(Dibromomethyl)-3-(tribromomethyl) hexane
(D) 1,1,4,4,4-Pentachloro-2,3-diethyl butane
2. The IUPAC name of the compound BrCH2 CHCl – CH – CH – CHBrCH2Cl is

CH3–CH2–CH2 CH2–CH2–CH2–CH3
(A) 4-(2-Bromo-1-chloroethyl)-5-(1-bromo-2-chloroethyl)nonane
(B) 1,5-Dibromo-2,6-dichloro-3,4-dipropylhexane
(C) 2,6-Dibromo-1,5-dichloro-3,4-dipropyl hexane
(D) None of these
CH3 CH3
3. The IUPAC name of the compound CH3–CH–CH–CH(CH2 CH2CH2CH3)2 is
(A) 4-Butyl-2,3-dimethyloctane (B) 1,1-Dibutyl-2,3-dimethylbutane
(C) 2,4-Dibutyl-3,3-dimethylbutane (D) None of these

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4. IUPAC name of the following compound

(A) 5-(2-methylpropyl)–5–(1,1–dimethylpropyl)nonane
(B) 5,5–Dibutyl-3,3,6-trimethylheptane
(C) 5–(1,1-dimethylbutyl)–5–(2–methylpropyl)nonane
(D) 5-butyl-4,4–Dimethyl–5–(2–methylpropyl)nonane
5. Name of the compound given below is

(A) 3-Methyl-4-ethyloctane (B) 2,3-Diethylheptane

(C) 5-Ethyl-6-methyloctane (D) 4-Ethyl-3-methyloctane
6. IUPAC name of the given compound
CH 3
|
CH 3  (CH 2 ) 4  CH  C  CH 2  CH 2  CH 3 is
| |
CH 3 CH 2  CH 3
(A) 4-Ethyl-4, 5-dimethyldecane (B) 3,4-Dimethyl-3-n-propylane
(C) 6, 7-Dimethyl-7-n-propynone (D) 6,7-Dimethyl-7-ethyldecane
7. The IUPAC name of the given structure H is
(A) 2,2-Dimethylbutane (B) Isohexane (C) 2,3-Dimethylbutane (D) Diisohexane

8. IUPAC name of the compound is :

(A) 5-methyl-4-isopropyl-6, 6-diethyloctane

(B) 3, 3-dimethyl-3-ethyl-5-isopropyloctane
(C) 3, 3-diethyl-4-methyl-5 (1, 1-dimethyl) octane
(D) 3, 3-diethyl-4-methyl-5 (1-methylethyl) octane
9. Write the IUPAC name of the following compound:
CH3 CH3
CH3 CH
CH3
(i) CH3 – C – CH – CH2 – CH2 – CH3 (ii) CH3 – CH2 – H2C – C – CH
CH3C2H5 CH3
CH
CH3 CH3

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CH3
(iii) CH3 – CH2 – CH – CH2 – CH2 – CH – CH2 – C – CH3

CH3 CHCH3 CH3

CH2CH3

C2H5 CH3 CH3

(iv) CH3 – CH2 – CH – C – CH2 – CH2 – CH – CH2 – CH2 – CH3

CH3 –C – CH3

CH3
10. Draw the structures of the following compounds
(i) 2, 3-Dimethyl-6-(1-methyl ethyl) decane
(ii) 5-(1, 1-Dimethyl ethyl)-6-ethyl-2-methyloctane

7. Rules in IUPAC nomenclature of unsaturated hydrocarbons

Alkenes and Alkynes
1. The parent chain must include the multiple bond regardless of the fact whether it is longest
continuous chain or not.
Example :
CH3 – CH2 – CH – CH2 – CH2 – CH3

CH = CH2
2. In writing the IUPAC name of a particular member of the alkene or alkyne family, the primary
suffix, ‘ane’ of corresponding in alkane is replacing by the correct ‘ene’ or ‘yne’ respectively.
3. The numbering of the parent chain must be done in such a way that the first C-atom
involved in the multiple bond gets the lowest number.
According to the latest IUPAC convention, the locants for the multiple bonds (double or
triple bonds) are placed immediately before the primary suffixes (ene or yne) which they
represent. The earlier practice was to place the locant either before the word root or after
the name of the primary suffix but it is not regarded as proper.
4 3 2 1
Example : CH3 – CH2 – CH = CH2
But-1-ene
4. If the selected principal or parent chain contains two (or three) double or triple bonds, then
the primary suffix -diyne (or triene) or -diene (or triyne) are used to represent these. In all
these cases, terminal ‘a’ is also added to the word root.

For example,

5. If the parent chain includes both double and triple bonds, then the following points must be
kept in mind.
(a) The unsaturated compound is always named as a derivative of alkyne i.e., primary
suffix ‘ene’ always comes before ‘yne’. In all such cases, the terminal ‘e’ of ‘ene’ is

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dropped if it is followed by the suffix starting with a, i, o, u or y.

Example :

(b) In case, the numbering from two different ends gives two different sets of locants,
then the lower set of locants is preferred.
5 4 3 2 1
Example : CH3 – CH = CH – C  CH
Pent-3-en-1-yne
6. If the unsaturated hydrocarbon contains a side chain (or substituent) along with the multiple
bonds, then the numbering of the parent or principal chain is done in such a way that the
multiple bonds gets the lowest set of locants. However, if the numbering from both ends
gives the same set of locants to the multiple bonds, then the locant for the substituent
must be minimum.

Example :

In some cases, more than two double bonds are present in the hydrocarbon and it is not
possible to include all of them in the parent chain. In such cases, the following prefixes
are used for the double bonded groups not involved in the chain.

Key Concept - 3

1. The IUPAC name of the given compound is :

(A) 4, 5-Dimethyl-4-octene (B) 4,5-Dimethyl-5-octene

(C) 3,4-Dimethyl-5-octene (D) 2,3-Dipropyl-2-butene
2. The IUPAC name of CH3C  CCH(CH3)2 is :
(A) 4-Methylpent -2- yne (B) 4,4-Dimethylpent -2- yne
(C) Methyl isopropyl acetylene (D) 2-Methylpent - 4 - yne
3. The IUPAC name of the compound CH3CH = CHCH = CHC  CCH3 is :
(A) 4,6-octadien-2-yne (B) 2,4-octadiene-6-yne
(C) 2-octyn-4, 5-diene (D) 6-octyn-2, 4-diene
4. The IUPAC name of the CH3 – CH = CH – C  CH is :
(A) 3-Penten-1-yne (B) 2-Penten-4-yne (C) 3-Pentyn-1-ene (D) 2-Pentyn-1-ene

CH 3
|
5. The IUPAC name of CH 3  C  CH  CH 2 is :
|
CH 3
(A) 2, 2,-Dimethyl-3-butene (B) 2,2-Dimethyl-4-pentene
(C) 3, 3-Dimethyl-1-Butene (D) 1-Hexene

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6. The IUPAC name of the compound is

Cl CH3
(A) 5-chloro 4-methyl hept-5-en-1-yne (B) 5-chloro 4-methyl hept-1-en-5-yne
(C) 3-chloro 4-methyl hept-2-en-6-yne (D) 3-chloro 4-methyl hept-6-en-2-yne

7. The IUPAC name of is :

Cl CH3 C2H5
(A) 6-Chloro-4-ethyl-5-methyl-5-hepten-1-yne
(B) 5-Methyl-4-ethyl-6-chloro-5-hepten-1-yne
(C) 6-Chloro-4-ethyl-5-methyl-1-hepten-5-yne
(D) 2-Chloro-4-ethyl-3-methyl-6-hepten-2-ene
8. The structure of trans-bis (ethenyl) ethene is

(A) (B) (C) (D)

9. Write the IUPAC name of the following compounds

CH3

(i) CHC–CH2–CH=CH–CH3 (ii)

CH3

(iii) H 3C  C  C  C  CH 3 (iv) H 3C  CH 2  CH 2  C  CH 2
| |
CH 3 ClH 2C  CH 2

(v) H 2C  CH  CH  CHCl CH  CH CH (CH 3 ) 2

|
CH (CH 3 )CH 2  CH 3

(vi) (CH3 )3 C – CH  C  C  C  CH2  CH2  CH(CH3 )2

|
CH2  CH  CH2

10. Draw the structures of the following compounds

(i) 3, 3, 6-Trimethyl-1, 4-heptadiene
(ii) 2-methyl-1,3-butadiene

8. IUPAC nomenclature of the cmpounds containing one

functional group or secondary suffix
1. Select the longest chain containing the carbon atom to which the maximum number of
functional group are attached. This is known as parent chain or principal chain. Where
the further rules are followed as mentioned earlier.
IUPAC names for compounds containing more than two similar terminal groups (special
cases)
If the organic compound contains more than two similar terminal groups and all of them
are directly attached to the parent or principal chain, then none of them forms a part of the
parent chain. Special suffixes are used to name these.

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ALCOHOL (R–O–H)
The fundamental portion of an alcohol is a hydroxy group connected to an alkyl group (R–
OH). The IUPAC names of alcohols are derived from the parent alkanes, but with ending
-ol. Replace - 'e' of the parent hydrocarbon by -ol.
Next step is to select a longest continuous chain containing C to which OH group is
attached. The C to which OH group is attached should get a minimum number.
CH3CH2OH CH3–CH2CHOH
Ethanol
CH3
butan-2-ol

1 2 3 4 5 6 7 8
CH3–CH2–CH–CH2–CH2–CH–CH2–CH3
OH CH3
The functional group present is an alcohol (OH). Hence the suffix is '–ol'.
The longest chain containing –OH has eight carbon atoms. Hence the corresponding
saturated hydrocarbon is octane.
The –OH is on carbon atom 3. In addition , a methyl group is attached at 6 th carbon.
Hence, the systematic name of this compound is: 6-Methyloctan-3-ol.
Alcohols, containing two ore more hydroxy groups are commonly known as polyhydric
alcohols and in IUPAC system, suffixes diol, triol, and so on are used instead of ol, to
indicate the number of hydroxyl groups. In such cases the vowel 'e' of alkane is retained
in the name. Thus, the general name for an alkane containing two hydroxyl group is
Alkanediol.
CH2–CH2 CH2–CH–CH2
OH OH OH OH OH
Ethane-1,2-diol Propane-1,2,3-triol
The unsaturated alcohols are named by replacing ane by suffix enol (ene + ol) or ynol
(yne + ol) of the corresponding alkanes.

1 2 3 4
CH3CH–CH=CH2
OH
But-3-en-2-ol

When a compound contains more than one functional group, the numbering and the suffix
in the name of multifunctional compound are determined by nomenclature priority.

ETHERS (R–O–R)
The general IUPAC name for ethers is alkoxyalkane.
The longer continuous carbon chain is named as alkane, whereas the chain with lesser
number of carbon atoms is named alkoxy and it always written as substituent with the
number specifying its position. For example

3 2 1
CH3–O–CH3 CH3OCH2CH3 CH3CHCH2OCH3
Methoxymethane Methoxyethane
CH3
1-methoxy-2-methylpropane

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The cyclic ethers are named as a prefix, which is commonly used for 3-membered cyclic
ethers. For example,
O
O H2C—C—CH2CH3
H2C—CH2
Epoxyethane
CH3
1,2-Epoxy-2-methylbutane

O
ALDEHYDES ( R—C—H or RCHO )
Aldehyde

The longest continuous carbon chain contains –CHO group and the carbon of –CHO
group gets the lowest number.
The aldehydes are named by suffixing al in place of e of the corresponding alkane. Thus
in general, an aldehyde is named as alkanal.
The chain is numbered from the aldehydic carbon but the position of the aldehyde is not
specific by number 'I', as it is understood that aldehydic carbon is the terminal carbon.
Compounds with two aldehydic groups are named Alkanedial and so on, where vowel 'e'
of alkane is retained.
The unsaturated aldehydes are named Alkenal (en + al) and Alkynal (yne + al)
4 3 2 1
CH3CH2CHO CHO CH3CH=CH–CHO
Propanal But-2-enal
CHO
Ethanedial

KETONE ( R–C– R or RCOR )

O
Ketone

The longest continuous carbon chain must contain ketonic group.

The ketones are named by suffixing one in place of e of the corresponding alkane. Thus,
the name Alkanone.
The carbon chain is numbered in such a way that ketonic group gets the lowest number.
Further, numbering the positions of the substituents is carried out and these are placed
as prefix according to the rules explained earlier.
The compounds containing two ketonic groups are termed as Alkanediones along with
the position number of groups. The vowel 'e' of the alkane is retained in this case.
The unsaturated ketones are called Alkanones (ene + one) or Alkynones (yne + one).
For example
O O
1 2 3 4 5 6
CH3CCH2CH3 CH3CH2–C–CHCH2CH2Cl
Butanone
Br O
4-Bromo-6-chlorohexan-3-one Pent-1-yne-3-one

O O
CH3–CH2–C–CH2–C–CH3

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CARBOXYLIC ACIDS (–COOH)

A carboxylic acid is an organic compound containing the carboxyl group
O
–C–O–H or –CO2Hor –COOH
The longest continuous carbon chain must contain the carboxylic group which gets the
lowest number.
The naming of carboxylic acids is done by adding the suffix oic acid in lieu of e of the
corresponding alkane. Thus, the name Alkanoic acid.
The name of carboxylic acid is written as two words (unlike others, written as single
word.)
The general name for the family of unsaturated carboxylic acid is Alkenoic acid and
Alkynoic acid.
In case of dicarboxylic acids, the longest chain should include both carboxylic groups.

CARBOXYLIC ACID DERIVATIVES

O O
(a) Acid anhydrides ( –C–O–C– )
Acid anhydride is name as Alkanoic anhydride, the name of anhydride is written as two
words.
An anhydride of a carboxylic acid has the structure of two carboxylic acid molecule with a
molecule of water removed.
(anhydride means without water).

O O O O
–H2O
CH3C—OH H—OC —CH3 CH3—C—O—C—CH3
an anhydride

If group is not symmetric with respect to oxygen than name both sided groups as alkanoic
alkanoic anhydride according to alphabetical order
O O
H3C–C–O–C–CH 2CH3
Ethanoic propanoic anhydride
(b) Esters (–COOR)
Esters are named as Alkyl alkanoates, where alkyl refers to alcoholic part and
alkanoate refers to carboxylic part of the molecules.
O O O

1 Alkanoic R—C—O—R Alkyl, H3C—C—O—CH3, H3C—C—O—CH2CH3

Methyl ethanoate Ethyl ethanoate

(c) Acid Halide (–COCl)

Acid halides are named as alkanoyl halides
CH 3COCl Ethanoyl chloride

(d) Acid Amides (–CONH2)

O
Acid amide are named as Alkanamides H3C–C–NH2
Ethanamide

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ALKYL CYANIDES (R –CN)
Alkyl cyanide is named as Alkanenitrile.
The longest chain must include the carbon of cyanide group (–CN) which gets the lowest
number.
2 1
CH3–CN Ethanenitrile

ALKYL ISOCYANIDES (R – NC)

Isocyanides are named as Alkaneisonitriles (earlier they were refereed to as carbylamine
derivatives.
The carbon of isonitrile is not included while selecting the parent chain. For example
CH3CH2NC Ethaneisonitrile
AMINES (R – NH2)
– NH2 group  1º amine.
The longest continuous carbon chain includes the carbon attached to –NH2 group.
Amines are named by suffixing amine in place of e of the corresponding alkane, Thus, the
general IUPAC name for amines is Alkanamine.
The example of primary amine 1
CH3
3 2 1 4 3 2 1 4 3 2
CH3CH2CH2NH2 CH3CH2CH2CH2NH2 CH3CH2CH–NH2
Propan-1-amine Butan-1-amine Butan-2-amine
The example of secondary and tertiary amines are as follows:
CH3
3 2 1
CH3CH2–CH2–NH–CH3 CH3CH2CH2–N–CH3
N-methylpropan-1-amine N,N-dimethylpropan-1-amine
(sec-amine) (ter-amine)
THIOALCOHOLS
The IUPAC name for thioalcohol is Alkanethiol
The lowest possible number is given to the carbon the – SH group . For example
CH3CH2SH Ethanethiol
SULPHONIC ACIDS
The longest continuous carbon chain includes the carbon having –SO3H group.
The general IUPAC name is given as Alkanesulphonic acid.
CH 3CH 2–CH 2SO 3H Propane-1-sulphonic acid

Note : When one type of the functional group are more than one than nomenclature can
be written by two types:

1. It may be noted that the carbon atoms of these terminal groups are not counted in the
principal or parent chain.
A few examples of such compounds are given :

CHO COOH
4 3 2 1 1 2 3
OCH – CH2 – CH2 – CH – CH2 – CHO HOOC – CH2 – CH – CH2 – COOH
Butane-1, 2, 4-tricarbaldehyde Propane-1,2,3-tricarboxylic acid

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CONH2
1 2 3 1 2 3
H2NOC – CH2 – CH – CH2 – CONH2
Propane-1, 2, 3-carbonitrile Propane-1, 2, 3-tricarboxamide

2. It may be noted that the carbon atoms of these terminal groups are counted in the principal
or parent chain.

CHO COOH
6 5 4 3 2 1 1 2 3 4 5
OCH – CH2 – CH2 – CH – CH2 – CHO HOOC – CH2 – CH – CH2 – COOH
3-formylhexan-1,6-dial 3-carboxypentane-1, 5-dioic acid

9. IUPAC nomenclature of the compounds containing more than

one different functional group of Poly functional compd.

Terminal characteristic group are those carbon containing groups which always occur at the end of
a chain. Terminal characteristic groups occur in carboxylic acids and their derivatives (esters, acyl
halides, amides, anhydrides etc.), aldehydes and cyanides. When the given organic compounds
contains two or more such similar groups, then exceptional treatment is given to such groups as
explained below.
1. When the given organic compound contains only two similar terminal groups: If the
given organic compound contains only two similar terminal groups, then principal chain is selected
in such a way that these two groups occur at the two ends of the principal chain. In such a case the
carbon atoms of both such group are counted in the principal chain and both such groups are
indicated by a suitable suffix along with the numerical prefix 'di'.
For example:
5 4 3 2 1 4 3 2 1
HOOC–CH2–CH2–CH2–COOH NH2CO–CH2–CH2–CONH2
Pentanedioic acid Butanediamide
CH3 OH
5 4 3 2 1 4 3 2 1
HOOC–CH2–CH2–CH2–COOH NH2CO–CH2–CH2–CONH2
2- Methylpentanedioic acid 2-Hydroxybutanediamide

5 4 3 2 1 4 3 2 1
C2H5OOC–CH2–CH2–CH2 –COOC2H5 ClOC–CH2–CH2–COCl
Diethylpentanedioate Butanedioyl chloride
5 4 3 2 1 5 4 3 2 1
N C–CH2–CH2–CH2–C N OHC–CH2–CH2–CH2–CHO
Pentanedinitrile Pentanedial

2. When the given organic compound contains more than two similar terminal groups : If
the given organic compound contains more than two similar terminal groups then the proce-
dure for its naming depends upon whether all such similar terminal groups are

To the principal chain : If the given organic compounds contains more than two similar terminal
groups and all such terminal groups are not directly attached to the principal chain, then the principal
chain selected is the longest chain with two such similar terminal groups its two ends. In such a case
other similar terminal groups are treated and indicated by suitable prefixes.

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 CH-11 NOMENCLATURE

CH2 –COOH
5 4 3 2 1
HOOC–CH2–CH2–CH2–COOH
3-(Carboxymeltyl)pentanedioic acid
CH2COOH
CH2COOC2H5
5 4 3 2 1
HOOC–CH2–C–CH2–COOH
C2H5OOC–CH2–CH2–CH2–COOC2H5 CH2COOH
Diethyl3–(ethoxycarbonylmethyl) pentanedioate
3,3-Bis(carboxymethyl)pentanedioic acid
(ii) If all similar terminal groups are directly attached to the principal chain. If the given
organic compound conatins more than two similar terminal groups and all such groups are directly
attached to the principal chain, then none of these groups forms a part of the principal chain. To name
such compounds special suffixes are used and when using these suffixes the carbon atoms of these
terminal groups are not counted in the principal chain. The special suffixes sued in these cases are
Groups Suffix
–COOH –carboxylic acid
–CHO –carbaldehyde
–CN –carbonitrile
–COX –carbonylhalide
–COOR R.......carboxylate
–CONH2 –carboxamide
This rule is illustrated by the following examples.
CHO
4 3 2 1
OHC–CH2 –CH2–CH–CH2–CHO
Butane-1,2,4-tricarbaldehyde

COOH
5 4 3 2 1
HOOC–CH2–CH 2–CH–CH2–CH2–COOH
Pentane-1,3,5-tricarboxylicacid

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FUNCTIONAL GROUPS IN DECREASING ORDER OF SENIORITY

Class Name Suffix Prefix

1. R–COOH Alkanoic acid – oic Acid (carboxylic acid) carboxyl

2. R–SO3H Alkane Sulphonic acid – sulphonic Acid sulpho

3. R–C–O–C–R Alkanoic Anhydride – anhydride ———

O O
4. R—COOR Alkyl alkanoate – alkanoate (carboxyliate) alkoxy carbonyl

5. R–C–X Alkanoyl halide – oyl halide (carbonyl halide) halo carbonyl

O
6. R–C–NH2 Alkanamide – amide (carboxamide) carbamoyl
O
Alkanenitrile – nitrile (carbonitrile) cyano

8. R–C–H Alkanal – al (carbaldehyde) formyl

O
9. R–C–R Alkanone – one Oxo / Keto
O
10. R–OH Alkanol – ol Hydroxy

11. R–SH Alkanethiol – thiol mercapto

12. R–NH2 Alkanamine – amine amino

Key Concept - 4
1. The IUPAC name of compound (CH3)3C.CH2CONH2 is
(A) 1,1,1-trimethyl propanamide (B) 3,3,3-trimethyl propanamide
(C) 3,3-dimethyl butanamide (D) 3-t-butyl propanamide

2. The IUPAC name of ethoxy--hydroxy propionic acid (trivial name) is

(A) 1,2-dihydroxy-1-oxo-3-ethoxy propane (B) 1-carboxy-2-ethoxy ethanol
(C) 3-Ethoxy-2-hydroxy propanoic acid (D) All above

OH Br
| |
3. The correct name for the compound CH 3  CH  CH 2  CH 2  CH  CHO

(A) 2-Bromo-5-hydroxyhexan-1-al (B) 1-Bromohydroxypentan-4-al

(C) 2-Hydroxy-5-bromohexan-6-al (D) None of the above

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4. The IUPAC name of the given compound

(A) 1-Chloro-4-methyl-2-hexanol (B)1-Chloro-2-hydroxy-4-methyl hexane

(C) 1-Chloro-4-methyl-2-pentanol (D) None
CHO CONH 2
| |
5. The IUPAC name of the given compound CH 3  CH  CH  CH  CH  COOH is :
| |
Br COCl
(A) 2-Bromo-4-carbamoyl-5-chloroformyl-3-formylhexanoic acid
(B) 5-Bromo-3-carbamoyl-2-chloroformyl-4-formylhexanoic acid
(C) 4-Formyl-2-chloroformyl-3-carbamoyl-5-bromohexanoic acid
(D) 2-Chloroformyl-3-carbamoyl-4-formyl-5-bromohexanoic acid
CH3
|
6. IUPAC name of CH 3  C  CH 2  CH  CH 3 is
| |
CH3 CN
(A) 2-Cyano-3-methylhexane (B) 2,4, 4-Trimethylpentanenitrile
(C) 2,2-Dimethyl-4-cyanopentane (D) 2-Cyano-3-methylhexane

Cl CO2H OH
Cl
7. Give the IUPAC name of the following compound :
Cl
O
(A) 3-4-Dichloro-6-[4-chloro-2-(hydroxymethyl)-5-oxohexyl] cyclohexane-1-carboxylic acid
(B) 4-5-Dichloro-2-[4-acetyl-4-chloro-2-(hydroxymethyl) buty] cyclohexane-1-carboxylic
acid
(C) 4-5-Dichloro-2-[4-chloro-2-(hydroxymethyl)-5-oxohexyl] cyclohexane-1-carboxylic acid
(D) None of these

8. The correct IUPAC name of compound having structural formula CH3 – CH(OH)–COOH
is
(A) Lactic acid (B) 2-hydroxy propanoic acid
(C) -hydroxy propanoic acid (D) carboxypropanol
9. The IUPAC name of the compound NH2 – CH – CH2OH is

COOH
(A) 1-amino-2-hydroxy propanoic acid (B) 2-amino-2-carboxy pentanol
(C) 2-amino-3-hydroxy propanoic acid (D) 1-hydroxy-2-amino-3 propanoic acid

10. Write the IUPAC name of the following compounds

CH3 CH2COOH
OH
(i) CH2=C–COOCH3 (ii) C
COOH
CH2COOH

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O COOH COOH
CH3–C=CH–CH2–C CH3–CH–CH2–CH–CH–CH2–COOH
(iii) (iv)
COOC2H5 OH CH2COOH

10. Nomenclature of atomatic compounds

Aromatic is regarded as aroma means pleasant smell. Aromatic compounds may be
classified into two main types. These are benzenoids and non-benzenoids.

(a) Benzenoids : These are cyclic compounds which contains in them either one or more
benzene rings. A few examples benzenoids are as follows.

Benzene Napthalene Anthrancene

It may be noted that the presence of double bonds in the alternate positions is note the
sole criteria for a compound to be aromatic. For example, cyclooctatetraene. (that contain
alternative single double bond but non aromatic)

Cyclooctatetraene
(b) Non-benzenoics : Certain compounds do not contain a benzene ring but they fulfil the
characteristics of aromatic compounds. These are called non-benzenoids. Some
heterocyclic compounds belongs to this class of aromatic compounds.
Example :

Certain ions can also behave as aromatic compound. For example

+
H

(c) Nomenclature of Benzenoids : Benzene (C6H6) is a hexagonal ring of carbon atoms

with single and double bonds in the alternate positions.
This ring is also called nucleus. In case any one or more hydrogen atoms attached to the
carbon atoms of the ring are substituted by some alkyl (R) groups or other functional
group then such groups form the side chains.

(d) Monosubstituted : Since all the carbon atoms in the ring are identical, by replacing a
hydrogen atom attached to any of them only one mono substituted derivative will be formed.

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Example :

(e) Disubstituted : A disubstituted derivative can be formed by substituting any of the five
available hydrogen atoms in the monosubstituted derivative by suitable substituents (x).
x

x
metaortho(or 1, 3)
(II)

It may be noted that the arabic numerals are used in the IUPAC names while the specific
prefixes ortho (o–), meta (m–), para(p-) are used for the common names. The aromatic
compounds are generally known by their common names or by commercial names in
some cases.
Tri and higher substituted – These are generally represented by the arabic numerals as
shown below
x
1
2

x 5 3 x
4
1, 3, 5-trisubstituted

Now let us write the IUPAC and common names (given in brackets) of a few important
members of different families of aromatic compounds.

I Aromatic hydrocarbons (arenes) :

The parent member is benzene and the substituted benzene derivatives are called arenes.

Aromatic hydrocarbons may also contain more than one ring either fused with each other
or attached by a covalent bond as shown below –

Naphthalene
In diphenyl, the two rings are linked by one single covalent bond, but in napthalene, are
fused at two adjacent position.

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II Aryl group :
An aryl group is obtained by removing one or more hydrogen atoms in the ring or side
chain.
Example :
–CH2 –CH –C–

Phenyl(C 6H5) Benzyl Benzal Benzo

III Halogen derivatives :

The halogen derivatives may be either nuclear substituted or side chain substituted
depending upon whether hydrogen atoms of the ring or the alkyl side chain have been
substituted.
Br
Cl 1
2 Br

Nuclear substituted :
1, 2-dibromobenzene
Chlorobenzene (o-Dibromobenzene)
3 2 1
CH2–Cl CH2 – CH2 – CH2Cl

Side chain substituted :

Chloro benzyl 1-chloro-3-phenyl propane

IV Hydroxy derivatives : The nuclear substituted hydroxy derivatives are called phenols
while the side substituted are known as aromatic alcohols.

OH

Phenol

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V Aldehydes :
2 1
CHO CH2–CHO 4 3 2
CH2– CH – CH2– CHO
1

Benzaldehyde 2-Phenylethanal
(Phenylacetaldehyde) 4-Phenylbutanal

VI Carboxylic acid :

COOH

Benzoic acid

VII Acid derivatives :

VIII Amines :

IX Ethers :

X Ketones :

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XI Nitro compounds :

XII Sulphonic acids :

XIII Cyanides & Isocyanides :

XIV Diazonium salts :

XV Grignard’s reagent –

Key Concept - 5

1. The IUPAC name of the compound is

(A) 2-isopropyl-3-methyl-1-phenyl-3-butanol (B) 3-isopropyl-2-methyl-4-phenyl-2-

butanol
(C) 3-benzyl-2, 4-dimethyl-4-pentanol (D) 3-benzyl-2, 4-dimethyl-4-pentanol

2. The IUPAC name of the following compound is :

(A) 4-chloro-1, 3-dinitrobenzene (B) 1-chloro-2, 4-dinitrobenzene

(C) 2, 4-dinitrobenzene chloride (D) 4-chloro benzene-2, 3-dinitrite]

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3. The IUPAc name of O2N CHO is:

OCH3
(A) 2-methoxy-4-nitro benzaldehyde (B) 4-nitro anisaldehyde
(C) 3-methoxy-4-formyl nitro benzene (D) 2-formyl-4-nitro anisole
O
4. The IUPAC name of C–CH3 is:

(A) phenyl ethanone (B) methyl phenyl ketone

(C) acetophenone (D) phenyl emethyl ketone
COOC2H5
5. The IUPAC name of is :
COCl
(A) 2-chlorocarbonyl ethylbenzoate (B) 2-carbocyethyl benzoyl chloride
(C) ethyl-2-(chlorocarbonyl) benzoate (D) ethyl-1-(chlorocarbonyl) benzoate

6. Write the IUPAC name of the following compound

(i) (ii)

(iii) (iv)

(v) (vi)

(vii) (viii)

(ix) (x)

11. Nomenclature of Alicyclic compounds

These compounds contain one or more rings of three or more carbon atoms and resemble
aliphatic compounds in their characteristics. These are, therefore, called aliphatic cyclic or
alicyclic compounds

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11.1 Monocyclic compounds :

The name of alicyclic compounds are based on the following rules.
I The names of the alicyclic compound are obtained by adding there primary prefix ‘cyclo’
to the word root that corresponds to the number of carbon atoms in the ring.
For the cyclic compounds containing all single bonds in the ring, primary suffix ‘ane’ is
added to the word root. For those containing one double or triple bond, the primary suffix
ene or yen is added.

II If only one substituent is attached to the ring, its position is note mentioned. If two or more
substituents are present, their positions are indicated by arabic numerals i.e., 1,2,3,4
........ etc. which are used for numbering the carbon atoms in the ring. The numbering is
done in such a way (clockwise or anticlockwise) that the substituents get the lowest set
of locants. All other rules relating to aliphatic or acyclic compounds are then followed. For
example.

III If a multiple bonds and some other substituents are present in the ring, the numbering is
done in such a way so as to assign lowest number to the multiple bond. For example
CH3
3
2 C2H5
1
2-Ethyl-3-methylcyclopent-1-ene
IV In case, some functional group along with some substituents are present in the ring, the
numbering of the carbon atoms should be done in such a way so that the functional group
gets lowest number.

In case, the functional group directly attached to the ring contains carbon atom, suitable
suffixes are used to represent such a group.
Functional group Suffix
– COOH Carboxylic acid
– CHO Carbaldehyde
–CN Carbonitrile
– COCl Carbonylchloride
– CONH2 Carboxamide
– COOR R—Carboxylate
A few example are given to represent these :

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COOH
1
2

3
NO2
3-Nitrocyclohex-2-ene-1-
carboxylic acid

V If the ring contains lesser carbon atoms than the alkyl group attached to it, the compound
is named as the derivative of alkane and the ring is treated as cycloalkyl substituent.
Otherwise, it is named as the derivative of cycloalkane. For example.

H3C – H2C – CH – CH3

Sec-Butylcyclohexane

In case, the side chain contains a multiple bond or a functional group, the alicyclic ring is
treated as the substituent irrespective of its size. For example,
3 2 1 3 2 1
H3C – CH – CHO CH2 – CH = CH2

2-Cyclohexylpropanal 3-Cyclopropylprop-1-ene
VI If the ring contains fewer carbon atoms than the alkyl group attached to it or when more
than one ring system is attached to a single chain the compound is named as a derivative
of alkane and the ring is treated as cycloalkyl substituent.
VII When both ring as well as side chain contains the same functional group, then the parent
hydrocarbon is decided on the basis of the number of carbon atom.
VIII If a compound contains an a cyclic ring as well as a benzene ring, it is named as a
derivative of benzene.

Key Concept - 6
OH

1. The IUPAC name of the compound is

OH
(A) 1, 2-dimethyl cyclo 3, 4-butenen-di-ol
(B) 1, 2-dihydroxy 3, 4-dimethyl cyclo but -3-ene
(C) 2, 3-dimethyl cyclo but -2-ene-1, 4-diol
(D) 3, 4-dimethyl cyclo but-3-ene-1, 2-diol

2. The IUPAC name of the given compound is : CH3

HO CH3
(A) 1, 1-dimethyl-3-hydroxy cyclohexane (B) 3,3-dimethyl-1-hydroxy cyclohexane
(C) 3,3-dimethyl-1-cyclohexanol (D) 1,1-dimethyl-3-cyclohexanol
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CH=CH–CHCH2CH3
3. The IUPAC name of
CH3
(A) 1-cyclohexyl-3-methyl-1-pentene (B) 3-methyl-5-cyclohexyl-pent-ene
(C) 1-cyclohexyl-3-ethyl-but-1-ene (D) 1-cyclohexyl-3, 4-dimethyl-but-1-ene

4. Give the IUPAC name of the following compound ,

(A) 2, 3-dimethyl cyclobuten-1 (B) 1, 2-dimethyl cyclobuten-1
(C) 1, 4-dimethyl cyclobuten-1 (D) 1, 2-dimethyl cyclobuten-2

5. The IUPAC name of the given compound is :

(A) 1,1 - dimethyl -3-hydroxy cyclohexane (B) 3, 3-dimethyl-1-hydroxy cyclohexane

(C) 3, 3-dimethyl-1-cyclohexanol (D) 1, 1-dimethyl-3-cyclohexanol
CH3

6. The correct IUPAC name of the compound is

H3C CH3
O
(A) 2, 4, 6-trimethyl cyclohexanone (B) 1, 3, 5-trimethyl benzophenone
(C) Trimethyl cyclobutanone (D) None

7. Give the IUPAC name of the following compound

(A) Octyl benzene (B) Octyl cyclo hexane

(C) 3-cyclohexyl octane (D) 3-phenyl octane

8. The correct IUPAC name of is

(A) 4-(2-Oxobutyl)cyclohexane-1-one (B) 2-(3-Oxobutyl)cyclohexane-1-one

(C) 1-(2-Oxocyclohexyl)butan-3-one (D) 4-(2-Oxocyclohexyl)butan-2-one

9. Write the IUPAC name of the following compounds

(i) (ii)

(iii) (iv)

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(v) (vi)

(vii) (viii)

11.2 IUPAC names of Polycyclic compounds

Certain cyclic compounds contain two or more rings . The IUPAC names of each
compounds are based upon the following guidelines .

I The carbon atoms common to the two rings are known as bridge head atoms . Each bond
or chain of carbon atoms which connects the bridge head atoms is known as bridge. The
bridge may contain either no carbon atom (0) or carbon atom (1) or two carbon atoms (2).
This may be illustrated by the following e.g.,

or

II The bicyclic compound is named by attaching the prefix ` bicyclo` to the name of the hydrocarbon
in which the root word contains the total number of carbon atoms involved in the two rings. The
number of the carbon atoms in the different bridges are represented by arabic numerals 0,1,2,3,
etc. These are arranged in a descending order separated by full stops [  ] and enclosed in square
brackets. The complete name of the hydrocarbon is written by placing the bracket between the
prefix and the name of the hydrocarbon.
For example,

Bicyclo [2.1.0 ] pentane

Bicyclo [3.3.0.] octane

If a substituent or double bond is present in one of the rings, then the bicyclic ring is numbered in

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order to ascertain its position. The numbering begins with one of the bridge head atoms, proceeds
first along the longest bridge to the seconds bridge head atoms, continues along the next longest
bridge to the first bridge head and finally ends at the substituted carbon along the shortest path.
For example,

2 Cl
3 1
8
4
6 7
5
8 - Chlorobicyclo [ 4.2.0 ] oct -2 - ene

RULE FOR IUPAC NOMENCLATURE OF SPIRO COMPOUNDS

If the two different rings have one common carbon atoms, the compounds are called spiro
compounds. Their name is prefixed by the word spiro followed by the bracket containing the
number of carbon atoms in asceding order, in each ring connecting to the common carbon
atom and then the name of the parent alkane containing the total number of carbon atoms in
the two rings. The positions of the substitutens are indicated by arabic numerals, the num-
bering starts form the ring atom next to the spiro atom and proceeding first from the smaller
ring and then to the spiro atom and finally around the largest ring. For example.
7 1 9 10 1
6 2

3 8 5
5 3
4 2 7 6 4
Spiro[2.4] heptane Spiro[4.5] decane

Carbon atoms in the two rings. The positions of the substitutens are indicated by arabic
numerals, the numbering starts from the ring atom next to the spiro atom and proceeding
first from the smaller ring and then to the spiro atom and finally around the largest ring. For
example.

7 1
CH3
9 10 1
Cl 6
2
3 8
5 5 3
4 2 7 6 4
6-chloro Spiro[2.4] heptane 10-methyl Spiro[4.5] decane

IUPAC Nomenclature of Unbranched Assemblies consisting of two or more identical

cyclic hydrocarbon units joined by a single Bond.
These systems are named by using a suitable numberals prefix such as bi (for two ) , tri (for
three), quarter (for four), quinque (for five) etc. before the name of the repetitive end, the carbon
atoms of each repetitive hydrocarbon unit are numbered with unpirmed and primed numbers
One unit is assigned unprimed and the other unit by primed, double primed etc.
3 4 4" 3"
1 1' 1' 2'
2 1 1" 2"
3 3' 4' 3'
1,1'-Bicyclopropane 1,1',2'1"-Tercyclobutane

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Key Concept - 7
O
1. The IUPAC name of the well known terpene camphor having the structure is

(A) 6-Oxo-1,2,2-trimethylbicyclo[2.2.1] heptane

(B) 1,7,7-Trimethyl bicyclo[2.2.1]heptan-2-one
(C) 1,5,5-Trimethylbicyclo[2.1.1] hexan-2-one
(D) 1,7,7-Trimethylbicyclo[2.1.2]heptan-2-one

2. IUPAC name of is

(A) Bicyclo [4.2.0] octane (B) Bicyclo [4.2.2] octane

(C) Bicyclo [6.2.0] octane (D) Bicyclo [4.2.2] octane

CH3

3. The IUPAC name of the compound, is

(A) 2-Methyl spiro [4.5] dec-1-ene (B) 2-Methyl spiro [5.4] dec-1-ene
(C) 2-Methyl spiro [4.5] dec-2-ene (D) 2-Methyl spiro [5.4] dec-2-ene

4. The IUPAC name of is

(A) Bicyclo [5.5.0] nonane (B) Biphenyl
(C) Cyclo propyl Cyclohexane (D) Spiro [2.5] octane

5. The IUPAC name of is

(A) Bicyclo [2.2.0] hexane (B) Spiro [2.2] hexane
(C) Spiro [2.2] pentane (D) none of these

6. The structure of spiro [3.3] heptane is

(A) (B) (C) (D)

7. The structure of bicyclo [1.1.0] butane is

(A) (B) (C) (D)

8. Draw the structures of the following compounds

(i) bicyclo [4,1,0] heptane
(ii) 7-methyl bicyclo[4,3,0]nonane
(iii) spiro[3,4]octane

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9. Write the IUPAC name of the following compounds.

(i) (ii)

(iii) (iv)

(v)

12. Some organic compounds with their common names:

S.No. General Name Formula IUPAC Name

1. Acetaldol or aldol 3-Hydroxybutanal

2. Acetanilide C6H5  NH  COCH3 N-phenyl ethanamide

3. Acetic anhydride CH3  CO  O  CO  CH3 Ethanoic anhydride

4. Acetoacetic ester CH3  CO  CH2  CO  O  C2H5 Ethyl - 3 - oxobutanoate
5. Acetylacetone CH3  CO  CH2  CO  CH3 2 , 4  Pentanedione
6. Acetophenone C6H5  CO  CH3 Acetylbenzene
7. Acrylaldehyde/acrolein CH2 = CH  CHO Propenal
8. Acrylic acid CH2 = CH  COOH Propenoic acid

9. Anthranilic acid 2 - amino benzoic acid

10. Allene CH2 = C = CH2 Propadiene

11. Allyl chloride CH2 = CH  CH2  Cl 3-chloropropene
OCH3

12. Anisole Methoxybenzene

13. n-amyl alcohol CH3 CH2 CH2 CH2 CH2 OH 1-pentanol

14. sec-amyl alcohol 3-pentanol

15. active-sec-amyl alcohol 2-pentanol

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16. Adipic acid Hexane - 1 , 6 - dioic acid

17. ter-amyl alcohol 2-methyl-2-butanol

18. Benzanilide C6H5  NH  CO  C6H5 N-phenyl benzamide

19. Benzene hexchloride C6H6Cl6 hexa chlorocyclohexane
or gemmexane

20. Carbamide or Urea NH2  CO  NH2 Aminomethanamide

21. Carbinol CH3  OH Methanol
22. Carbolic acid C6H5OH Phenol
S.No. General Name Formula IUPAC Name

23. Chloral CCl3  CHO Trichloroethanal

24. Catechol Dihydroxy benzene

2,2,2-trichloro-1,
25. Chloral hydrate
1-ethanediol

1,1,1-trichloro-2-
26. Chloretone methyl-2-propanol
27. Chloropicrin CCl3  NO2 Trichloronitromethane
28. Chloroprene 2-chloro-1, 3-butadiene

29. Cinnamaldehyde C6H5  CH = CH  CHO 3-phenylpropenal

30. Cinnamyl alcohol C6H5  CH = CH  CH2  OH3-phenyl-2-propen-1-ol
31. Cinnamic acid C6H5  CH = CH  COOH 3-phenyl-2-
propenoic
acid
OH
2-hydroxy-1,2,3–
32. Citric acid HOOC–CH2–C–CH2–COOH propanetri-carboxylic
acid
COOH
33. Crotonic acid (trans) CH3  CH = CH  COOH 2 - butenoic acid
34. Crotonaldehyde CH3  CH = CH  CHO 2 - butenal
35. Crotyl alcohol CH3  CH = CH  CH2  OH 2-buten-1-ol
36. Freon - 11 CFCl 3 Trichlorofluromethane
37. Freon - 12 CF 2Cl 2 Dichlorodifluoroethane
38. Freon - 112 C2F 2Cl4 1 , 1 , 2 , 2 - Tetrachloro - 1 ,
2

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 CH-11 NOMENCLATURE
- difluoroethane
39. Fumaric acid trans-butenedioc acid

40. Glyceraldehyde 2 , 3 - dihydroxypropanal

41. Glycerine or Glycerol 1 , 2 , 3 - Propanetriol

42. Glycol 1 , 2 - ethanediol

S.No. General Name Formula IUPAC Name

43. Glyoxal ethanedial

44. Glutaric acid Pentane - 1 , 5 - dioic acid

45. Glycollic acid HO  CH2  COOH 2-hydroxyethanoic acid

46. Lactic acid 2-hydroxypropanoic acid

47. Malonic acid Propane-1 , 3-dioic acid

OH
COOCH3
methyl-2-hydroxy
48. Oil of winter green benzenecarboxylate

49. Oxalic acid Ethane-1 , 2-dioic acid

OH
O2N NO2

50. Picric acid 2,4,6-Trinitrophenol

NO2

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 CH-11 NOMENCLATURE

CH=CH2
Phenyl ethene
51. Styrene or Ethenylbenzene

52. Succinic acid Butane-1 , 4-dioic acid

NH2

53. Toluidine CH3 2-methylaniline

CH3

CH3–C–––CH–CH3
54. Triptane 2,2,3-trimethylbutane
CH3 CH3

55. Stilbene Ph–CH=CH–Ph

Key Concept - 8

1. The IUPAC name for is:

(A) 6-Ethyl-3,4-dimethylheptane (B)2-Ethyl-4,5-dimethylheptane

(C) 3,4,6-Trimethyloctane (D) 3,5,6-Trimethyloctane

2. An IUPAC name for is:

(A) 5-Methyl-4-(1-methylpropyl)hexane (B) 2-Methyl-3-(1-methylpropyl)hexane

(C) 2-Methyl-3-(2-methylpropyl)hexane (D) 3-Methyl-4-(1-methylethyl)heptane

3. A correct IUPAC name for the following compound is:

(A) 2,5-Dimethyl-3-propylheptane (B) 3,6-Dimethyl-5-propylheptane

(C) 6-Methyl-4-(1-methylethyl)octane (D) 3-Methyl-5-(1-methylethyl)octane

4. A correct IUPAC name for the following compound is:

OH Cl
(A) 4-propyl-5-chloro-3-heptanol (B) 4-propyl-3-chloro-5-heptanol
(C) 4-(1-chloropropyl)-3-heptanol (D) 5-chloro-4-propyl-3-heptanol

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 CH-11 NOMENCLATURE
5. Which is the correct name for the compound shown below?

(A) Bicyclo[2.2.0]hexane (B) Bicyclo[2.2.0]butane

(C) Bicyclo[2.2.2]hexane (D) Bicyclo[2.2.1]hexane

6. What is the name of this compound?

(A) Bicyclo[2.2.2]octane (B) Bicyclo[3.2.1]octane

(C) Bicyclo[4.1.1]octane (D) Bicyclo[4.2.0]octane

Br
7. What is the common name for this compound?

(A) Isobutyl bromide (B) tert-Butyl bromide (C) Butyl bromide (D) sec-Butyl bromide

8. A correct IUPAC name for the following compound is:

Br

(A) 3,6,7-trimethyl-4-bromo-1-octene (B) 4-bromo-3-methyl-6-isopropyl-1-heptene

(C) 4-bromo-3,6,7-trimethyl-1-octene (D) 4-bromo-6-isopropyl-3-methyl-1-heptene

9. A correct name for the following compound is:

(A) 2-Methylbicyclo[4.3.0]nonane (B) 1-Methylbicyclo[4.3.1]nonane

(C) 7-Methylbicyclo[4.3.0]nonane (D) 2-Methylbicyclo[4.3.1]nonane

Use the following to answer questions 10-12:

I II III IV V
10. Which of the above is bicyclo[3.3.1]nonane?
(A) I (B) II (C) III (D) IV

11. Which of the above is bicyclo[5.2.0]nonane?

(A) I (B) II (C) III (D) V

12. Which of the above is bicyclo[4.3.0]nonane?

(A) I (B) II (C) III (D) IV

13. An IUPAC name for the group CH3CHCH2 is:

CH2CH3
(A) Isopentyl (B) Isoamyl (C) sec-Butylmethyl (D) 2-Methylbutyl

14. The neopentyl group has the alternative name:

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 CH-11 NOMENCLATURE
(A) 1,1-Dimethylpropyl (B) 1,2-Dimethylpropyl
(C) 2,2-Dimethylpropyl (D) 1-Methylbutyl
Br
15. The correct IUPAC name for is:
Cl
(A) 2-Bromo-4-chloro-4-isopropylpentane (B) 4-Bromo-2-chloro-2-isopropylpentane
(C) 5-Bromo-3-chloro-2,3-dimethylhexane (D) 2-Bromo-4-chloro-4,5-dimethylhexane

16. Which of the following is a correct name which corresponds to the common name tert-
pentyl alcohol?
(A) 2,2-Dimethyl-1-propanol (B) 2-Ethyl-2-propanol
(C) 2-Methyl-2-butanol (D) 3-Methyl-1-butanol

17. The correct IUPAC name for the following compound is:
OH

(A) 1-Hydroxy-3-sec-butylcyclopentane (B) 3-sec-Butyl-1-cyclopentanol

(C) 1-sec-Butyl-3-cyclopentanol (D) 4-sec-Butyl-1-cyclopentanol

18. What is a correct name for the following compound?

(A) 3-Isobutyl-2-methylheptane (B) 3-sec-Butyl-2-methyloctane

(C) 5-Isobutyl-6-methylheptane (D) 4-Isopropyl-3-methylnonane
19. What is the correct name of the following compound?
Cl

(A) 1-Chlorobicyclo[4.1.1]octane (B) 2-Chlorobicyclo[4.1.0]octane

(C) 2-Chlorobicyclo[4.1.1]octane (D) 2-Chlorobicyclo[4.1.1]heptane

20. What is the correct IUPAC name for the following compound?

HO
(A) 3-Hydroxymethylheptane (B) 3-Hydroxymethylhexane
(C) 3-Methyloxyheptane (D) 2-Ethyl-1-hexanol

21. Which of the following structures represents bicyclo[3.2.1]octane?

I II III IV V
(A) I (B) II (C) III (D) V

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 CH-11 NOMENCLATURE

22. Which of these is the common name for the 1,1-dimethylpropyl group?
(A) tert-Butyl (B) tert-Pentyl (C) Isopentyl (D) Neopentyl

23. Neglecting stereochemistry, which of these common group names is ambiguous, i.e.,
does not refer to one specific group?
(A) Butyl (B) sec-Butyl (C) tert-Pentyl (D) sec-Pentyl

24. What is the correct IUPAC name for the following compound?
OH

(A) 5-Ethyl-3-methylhexanol (B) 5-Ethyl-3-methyl-1-hexanol

(C) 2-Ethyl-4-methyl-6-hexanol (D) 3,5-Dimethyl-1-heptanol

25. Isopentyl is the common name for which alkyl group?

(A) CH3CH2CH2CH (B) CH3CH2CHCH2
CH3 CH3
(C) CH3CHCH2CH2 (D) CH3CH2CH

CH3 CH2CH3

26. An IUPAC name for is:

(A) 3-Isobutyl-2,4-dimethylhexane (B) 3-sec-Butyl-2,5-dimethylhexane

(C) 4-sec-Butyl-2,5-dimethylhexane (D) 4-Isopropyl-2,5-dimethylheptane

27. An IUPAC name for the following compound is:

(A) 4-Isobutyl-3,4-dimethylheptane (B) 4-sec-Butyl-2,4-dimethylheptane

(C) 2,4,5-Trimethyl-4-propylheptane (D) 3,4,6-Trimethyl-4-propylheptane

28. What is the correct IUPAC name for the following compound?

HO
(A) 3-Hydroxymethyl-2-heptene (B) 2-(1-methylethyl)-4-hexen-1-ol
(C) 5-(1-methylethyl)-2-hexen-6-ol (D) 5-isopropyl-2,6-hexenol

29. What is the correct IUPAC name for the following compound?
OH

(A) 5-Ethyl-3-fluorohexanol (B) 5-Ethyl-3-fluoro-1-hexanol

(C) 2-Ethyl-4-fluoro-6-hexanol (D) 3-fluoro-5-methyl-1-heptanol

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 CH-11 NOMENCLATURE

30. A correct name for the following compound is:

Cl
(A) 3-chloro-8-methylbicyclo[4.3.0]nonane (B) 8-Methyl-3-chlorobicyclo[4.3.1]nonane
(C) 3-Methyl-7-chlorobicyclo[4.3.0]nonane (D) 3-Methyl-7-chlorobicyclo[4.3.1]decane

31. A correct name for the following compound is: Br

(A) 4-bromo-3,8-dimethylbicyclo[5.2.2]nonane
(B) 3,8-dimethyl-4-bromo-bicyclo[5.2.0]nonane
(C) 4-bromo-3,8-dimethylbicyclo[5.2.1]decane
(D) 4-bromo-3,8-dimethylbicyclo[5.2.0]nonane

ANSWER KEY

Key Concept - 1

1. C 2. B 3. C 4. D 5. A
6. (a) 1 – 3º carbon (b) 3 – 1º carbon 7. (a) 1 (b) 1
8. 1ºC 6, 2ºC 2, 3ºC 2, 4ºC 1,
9. 1ºC 5, 2ºC 1, 3ºC 1, 4ºC 1

CH3 CH3 H2C CH2 CH3

10. CH3–C–—C–CH3 11. H2C CH2 12. CH3–CH–CH–CH3

CH3 CH3 H2C CH2 CH3

Key Concept - 2
1. A 2. A 3. A 4. D 5. D 6. A
7. C 8. D
9. (i) 3-ethyl-2,2-dimethylhexane (ii) 3,3-di[1-methylethyl]2-methylhexane
(iii) 4-[1-methylpropyl]-2,2,7-trimethylnonane
(iv) 4-[1,1-dimethylethyl]-3-ethyl-4,7-dimethyldecane
CH3
CH–CH3
10. (a) CH3–CH–CH–CH2–CH2–CH–CH2–CH2–CH2–CH3
CH3 CH3
CH2–CH3
(b) H3C–CH–CH2–CH2–CH–CH–CH2–CH3
CH3 CH3–C–CH3
CH3

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 CH-11 NOMENCLATURE

Key Concept - 3
1. A 2. A 3. B 4. A 5. C 6. A
7. A 8. B
9. (i) Hex-4-en-1-yne (ii) 3,3-dimethylpent-1-en-4-yne
(iii) 4-methylpent-2-yne (iv) 2-[2'-chloroethyl]pent-1-ene
(v) 4-chloro-3-[1'-methylpropyl]-7-methylocta-1,5-diene
(vi) 4-allyl-2,2-9,-trimethyldec-3-en-5-yne
CH3 CH3

10. (a) H2C=CH–C–CH=CH–CH–CH3 (b) H2C=C–CH=CH2

CH3 CH3
Key Concept - 4

1. C 2. C 3. A 4. A 5. B 6. B
7. C 8. B 9. C
10. (i) Methyl 2-methyl prop-2-enoate
(ii) 2-hydroxypropane-1,2,3-tricarboxylic acid
(iii) 4-ethoxycarbonylpent-3-ene-1-oic acid
(iv) 3-(carboxymethyl) hexane-1,2,5-tricarboxylic acid

Key Concept - 5

1. B 2. B 3. A 4. A 5. C
6. (i) Methyl-benzoate (ii) 2-amino-1-phenylpropane
(iii) 3-phenylprop-2-en-1-al (iv) Ethoxy-4'-methylbenzene
(v) 2,4-difluorobenzene sulphonic acid (vi) Benzenoyl chloride
(vii) 1-phenylprop-1-one (viii) 4-phenyl,4-ketobutan-1-oic acid
(ix) 4-phenylbutane-1-oyl chloride (x) N-pehnyl ethanamide

Key Concept - 6
1. D 2. C 3. A 4. A 5. C 6. A
7. D 8. B
9. (i) 1-ethyl 3-methylcyclohexane (ii) 4-ethyl 2-methylcyclohex-1-ene
(iii) 3-cyclohexyl prop-1-ene (iv) 3-hydorxycyclohexanone
(v) 1-chloro, 2-cyclohex-3-ene-butane (vi) 2-cyclopentyl hexane
(vii) 1-Amido-2-methylcyclopentane
(viii) 5-amino-6-[1-methylpropyl]cyclohex-2-en-1-ol]

Key Concept - 7
1. B 2. A 3. A 4. D 5. C 6. B

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 CH-11 NOMENCLATURE

7. D 8. (i) (ii) CH3 (iii)

9. (i) Bicyclo-[3.1.0]hexane (ii) 9,9-dimethylbicyclo[4.2.1]nonane

(iii) Bicyclo[2.2.2]ocatane (iv) 8-chlorobicyclo[4.2.0]octane
(v) Bicyclo[2.1.0]pentane

Key Concept - 8
1. C 2. D 3. D 4. D 5. A 6. D
7. A 8. C 9. A 10. D 11. D 12. A
13. D 14. C 15. C 16. C 17. B 18. D
19. C 20. D 21. D 22. B 23. D 24. D
25. C 26. D 27. C 28. B 29. D 30. A
31. D

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 CH-11 NOMENCLATURE

EXERCISE - 1
SINGLE CHOICE CORRECT TYPE QUESTIONS
1 How many 1°carbon atom will be present in a simplest hydrocarbon having two 3° and one 2°
carbon atom?
(A) 3 (B) 4 (C) 5 (D) 6

2 How many carbons are in simplest alkyne having two side chains?
(A) 5 (B) 6 (C) 7 (D) 8

3 Which of the following pairs have absence of carbocyclic ring in both compounds?
(A) Pyridine, Benzene (B) Benzene, Cyclohexane
(C) Cyclohexane, Furane (D) Furane, Pyridine

4 The commercial name of trichloroethene is:

(A) Westron (B) Perclene (C) Westrosol (D) Orlone

5 How many secondary carbon atoms does methyl cyclopropane have?

(A) None (B) One (C) Two (D) Three

6 The compound which has one isopropyl group is:

(A) 2,2,3,3-Tetramethyl pentane (B) 2,2-Dimethyl pentane
(C) 2,2,3-Trimethyl pentane (D) 2-Methyl pentane

7 Which of the following is the first member of ester homologous series?

(A) Ethyl ethanoate (B) Methyl ethanoate
(C) Methyl methanoate (D) Ethyl methanoate

8 The group of heterocylic compounds is:

(A) Phenol, Furane (B) Furane, Thiophene
(C) Thiophene, Phenol (D) Furane, Aniline

9 and

Number of secondary carbon atoms present in the above compounds are respectively:
(A) 6,4,5 (B) 4,5,6 (C) 5,4,6 (D) 6,2,1

10 A substance containing an equal number of primary, secondary and tertiary carbon atoms is:
(A) Mesityl Oxide (B) Mesitylene (C) Maleic acid (D) Malonic acid

11 The molecular formula of the first member of the family of alkenynes and its name is given by
the set
(A) C3H2, Alkene (B) C5H6, Pent-1-en-3-yne
(C) C6H8, Hex-1-en-5-yne (D) C4H4, Butenyne

12 Which of the following is a heterocyclic compound

HC  CH HC  COOH HC  CH HC  CH
(A) | S (B) | (C) | (D) |
HC  CH HC  COOH HC  CH HC  CH

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 CH-11 NOMENCLATURE

CH 3 CH 3
| |
13 The correct IUPAC name of the compound CH 3  CH 2  C  C  CH  C  CH 2  CH 2  CH 3 :
|
C2H5
(A) 5-Ethyl-3, 6-dimethyl non-3-ene (B) 5-Ethyl-4, 7-dimethyl non-3-ene
(C) 4-Methyl-5, 7-diethyl oct-2-ene (D) 2,4-Ethyl-5-methyl oct-2-ene

14 The IUPAC name of CH  CH  CHCH 2CH 3 is:

|
CH 3
(A) 1-Cyclohexyl-3-methylpent-1-ene (B) 3-Methyl-5-cyclohexylpent-1-ene
(C) 1-Cyclohexyl-3-ethylbut-1-ene (D) 1-Cyclohexyl-3,4-dmethyl-but-1-ene

15 IUPAC name of is:

(A) But-2-ene-2,3-diol (B)Pent-2-ene-2,3-diol

(C) 2-Methylbut-2-ene-2,3-diol (D) Pent-3-ene-3,4-diol

16 IUPAC name of is:

(A) 5-Methyl hexanol (B) 2-Methyl hexanol

(C) 2-Methyl hex-3-enol (D) 4-Methyl pent-2-enol

17 The IUPAC name of CH 3 CH 2  N  CH 2CH 3 is:

|
CH 3
(A) N-Methyl-N-ethyl ethanamine (B) Diethyl methanamine
(C) N-Ethyl-N-methyl ethanamine (D) Methyl diethyl ethanamine

18 The IUPAC name of acetyl acetone is:

(A) Pentane-2,5- dione (B)Pentane -2,4-dione
(C) Hexane-2,4-dione (D)Butane-2,4-dione

19 When vinyl & allyl are joined each other, we get

(A) Conjugated alkadiene (B) comulative alkadiene
(C) Isolated alkadiene (D) Allenes

20 (a) and (b)

True statement for the above compounds is:

(A) (a) is phenol while (b) is alcohol (B) Both (a) and (b) are primary alcohol
(C) (a) is primary and (b) is secondary alcohol (D) (a) is secondary and (b) is primary
alcohol
21 The IUPAC name of the following structure (CH3)C.C.C.(CH3)CH(CH3) is:
(A) 3-Methylhex-4-yn-2-ene (B) 3-Methylhex-2-en-4-yne
(C) 4-Methylhex-4-en-4-yne (D) all are correct

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 CH-11 NOMENCLATURE

22 The IUPAC name of the following structure is [CH3CH(CH3)]2 C(CH2CH3)C(CH3) C(CH2CH3)2

(A) 3,5-Diethyl-4,6-dimethyl-5-[1-methylethyl]hept-3-ene
(B) 3,5-Diethyl-5-isopropyl-4,6-dimethylhept-2-ene
(C) 3,5-Diethyl-5-propyl-4,6-dimethylhept-3-ene
(D) None of these

23 The correct IUPAC name of CH 3  CH 2  C  COOH is:

||
CH 2
(A) 2-Methyl butanoic acid (B) 2-Ethylprop-2-enoic acid
(C) 2-Carboxybutene (D) None of the above

24 The correct IUPAC name of 2-ethylpent-3-yne is:

(A) 3-Methyl hex-4-yne (B) 4-Ethyl pent-2-yne
(C) 4-methyl hex-2 yne (D) None of these

25 The IUPAC name of the compound Glycerire CH 2  CH  CH 2 is:

| | |
OH OH OH
(A) 1,2,3-Tri hydroxy propane (B) 3-Hydroxy pentane-1,5-diol
(C) 1,2,3-Hydroxy propane (D) Propane-1,2,3-triol

26 All the following IUPAC names are correct except:

(A) 1-Chloro-1-ethoxy propane (B) 1-Amino-1-ethoxypropane
(C) 1-Ethoxy-2-propanol (D) 1-Ethoxy-1-propanamine

27 The IUPAC name of the compound CH3CH = CHCH=CHCCCH3 is:

(A)Octa-4,6-diene-2-yne (B)Octa-2,4-diene-6-yne
(C) Oct-2-yne-4,6-diene (D) Oct-6-yne-2,4-diene

28 C3H6Br2 can shows:

(A) Two gem dibromide (B) Three vic dibromide
(C) Two tert. dibromo alkane (D) Two sec. dibromo alkane

29 The IUPAC name of -ethoxy--hydroxy propionic acid (trivial name) is:

(A) 1,2-Dihydroxy-1-oxo-3-ethoxy propane (B) 1-Carboxy-2-ethoxy ethanol
(C) 3-Ethoxy-2-hydroxy propanoic acid (D) All above

30 As per IUPAC rules, which one of the following groups, will be regarded as the principal functional
group?
(A) –CC– (B) –OH (C)  C  (D)  C  H
|| ||
O O
31 The IUPAC name of the compound Br(Cl) CI. CF3 is:
(A) 2-Bromo-2-chloro-2-iodo1,1,1-trifluoroethane
(B) 1,1,1-Trifluoro-2-bromo-2-chloro-2-iodo ethane
(C) 2-Bromo-2-chloro-1,1,1-trifluoro-2-iodo ethane
(D) 1-Bromo-1-chloro-2,2,2-trifloro-1-iodo ethane

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 CH-11 NOMENCLATURE

32 The IUPAC name of the given compound is:

(A) 1,1-Dimethyl-3-hydroxy cyclohexane (B) 3,3-Dimethyl-1-hydroxy cyclohexane

(C) 3,3-Dimethylcyclohexanol (D) 1,1-Dimethylcyclohexan-3-ol
33 The IUPAC name of (C2H5)2 NCH 2 CH.COOH is:
|
Cl
(A) 2-Chloro-4-N-ethylpentanoic acid (B) 2-Chloro-3-(N,N-diethyl amino)-propanoic acid
(C) 2-Chloro-2-oxo diethylamine (D) 2-Chloro-2-carboxy-N-ethyl ethane

Ph
|
34 The IUPAC name of the compound is CH 3  CH  CH  NH 2
|
CH 3
(A) 1-Amino-1-phenyl-2-methyl propane (B) 2-Methyl-1-phenyl propan-1-amine
(C) 2-Methyl-1-amino-1-phenyl propane (D) 1-Isopropyl-1-phenyl methyl amine

35 Which of the following compound is wrongly named?

(A) CH 3CH 2 CH 2 CHCOOH ; 2-Chloro pentanoic acid
|
Cl

(B) CH 3C  CCHCOOH ; 2-Methyl hex-3-enoic acid

|
CH 3
(C) CH3CH2CH=CHCOCH3 ; Hex-3-en-2-one
(D) CH 3  CHCH 2CH 2CHO ; 4-Methyl pentanal
|
CH 3

36 The correct IUPAC name of the following compound is:

O  C  CH 2  CH  CHO
| |
OH H  C  O
(A) 3,3-Diformylpropanoic acid (B) 3-Formyl-4-oxo-butanoic acid
(C) 3,3-Dioxo propanoic acid (D) 3,3-Dicarbaldehyde propanoic acid
37 The correct IUPAC name of compound:

CH 3  CH 2  C  CH  CHO
|| | is:
O CN
(A) 2-Cyano-3-oxopentanal (B) 2-Formyl-3-oxopentanenitrile
(C) 2-Cyanopentane-1,3-dione (D) 1,3-Dioxo-2-cyanopentane

38 IUPAC name of:

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 CH-11 NOMENCLATURE

CH 3  C  CH  C  OCH 3
|| | ||
O C O O
|
CH 3
(A) Methyl 2,2-bis(1-oxoethyl)ethanoate
(B) 2,2 -Bis(1-oxoethyl)-1-methoxy ethanone
(C) Methyl 2-(1-oxoethyl)-3-oxobutanoate
(D) Methyl 2-acetyl-3-oxo butanoate

O CH 3
|| |
39 The IUPAC name of compound CH  C  CH  CH  CH  CH is:
3 3
| |
CH 3 CHO
(A) 3,5-Dimethyl-4-Formyl pentanone (B) 1-Isopropyl-2-methyl-4-oxo butanal
(C) 2-Isopropyl-3-methyl-4-oxo pentanal (D) None of the above

HO  C  O CH 3
| |
40 The IUPAC name of compound CH 3  C  C — C  H is:
| |
NH 2 Cl
(A) 2-Amino-3-chloro-2-methylpent-2-enoic acid
(B) 3-Amino-4-chloro-2-methylpent-2-enoic acid
(C) 4-Amino-3-chloro-2-methylpent-2-enoic acid
(D) All of the above

41 The IUPAC name of the structure is:

H 2 N  CH  CH  CHO
| |
HOOC COOH
(A) 3-Amino-2-formyl butane-1, 4-dioic acid
(B) 3-Amino-2, 3-dicarboxy propanal
(C) 2-Amino-3-formyl butane-1, 4-dioic acid
(D) 1-Amino-2-formyl succinic acid
42 One among the following is the correct IUPAC name of the compound
H
|
CH 3CH 2  N  CHO
(A) N-Formyl aminoethane (B) N-Ethyl formyl amine
(C) N-Ethyl methanamide (D) Ethylamino methanal

43 The number of primary, secondary and tertiary amines possible with the molecular fomula
C3H9N is:
(A) 1,2,2 (B) 1,2,1 (C) 2,1,1 (D) 3,0,1

44 The IUPAC name of C6H5CH=CH–COOH is:

(A) Cinnamic acid (B) 1-Phenyl-2-carboxy ethane
(C) 3-Phenyl prop-2-enoic acid (D) Dihydroxy-3-phenyl propionic acid

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 CH-11 NOMENCLATURE

45 The IUPAC name of BrCH 2  CH  CO  CH 2  CH 2CH 3 is:

|
CONH 2
(A) 2-Bromomethyl-3-oxohexanamide (B) 1-Bromo-2-amino-3-oxohexane
(C) 1-Bromo-2-amino-n-propyl ketone (D) 3-Bromo-2-propyl propanamide

46 IUPAC name will be CH 2  CH  CH 2

| | |
CN CN CN
(A) 1,2,3-Tricyano propane (B) Propane-1,2,3- trinitrile
(C) 1,2,3-Cyano propane (D) Propane-1,2,3-tricarbonitrile

47 The IUPAC name of compound

(A) 1,2,3-Tricarboxypropan-2-ol
(B) 2-Hydroxy propane-1,2,3- tricarboxylic acid
(C) 3-Hydroxy-3-carboxypentane-1,5-dioic acid
(D) None
48 The IUPAC name of CH 3  C  O  CH 2  C  OH is:
|| ||
O O
(A) 1-Acetoxy acetic acid (B) 2-Acetoxy ethanoic acid
(C) 2-Ethanoyloxyacetic acid (D) 2-Ethanoyloxyethanoic acid

49 CH 3  O  C  CH 2  COOH
||
O
The correct IUPAC systematic name of the above compound is:
(A) 2-Acetoxy ethanoic acid (B) 2-Methoxy carbonyl ethanoic acid
(C) 3-Methoxy formyl ethanoic acid (D) 2-Methoxy formyl acetic acid

50 The IUPAC name of is

(A) 3-Methyl cyclobut-1-ene-2-ol (B) 4-Methyl cyclobut-2-ene-1-ol

(C) 4-Methyl cyclobut-1-ene-3-ol (D) 2-Methyl cyclobut-3-ene-1-ol

51 The IUPAC name of is:

(A) 2-Methoxy-4-nitro benzaldehyde (B) 4-Nitro anisaldehyde

(C) 3-Methoxy-4-formyl nitro benzene (D) 2-Formyl-4-nitro anisole

52 The IUPAC name of compound

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 CH-11 NOMENCLATURE

H 3COOC  CH  COOCH3
|
CH 2OH
(A) 2-(Hydroxy methyl) methyl propanedioate
(B) Methyl-2-(hydroxy methyl) propanedioate
(C) 2-(Hydroxy methyl) dimethyl propanedioate
(D) None of these

53 The suffix of the principal group, the prefixes for the other groups and the name of the parent in
the structure
HO  CH 2  CH  CH  C  CH 2  C  C  OH
| | || ||
CH 3 Cl O O
(A) -oic acid, chloro, hydroxy, oxo, methyl, hept-4-ene
(B) -oic acid, chloro, hydroxy, methyl, oxo, hept-4-ene
(C) -one, carboxy, chloro. methyl, hydroxy, hept-4-ene
(D) -one, carboxy, chloro, methyl, hydroxy, hept-4-ene

CH 2  CHO
|
54 The IUPAC name of OHC  CH 2  CH 2  CH  CH 2  CHO is:
(A) 4,4-Di(formylmethyl) butanal (B) 2-(Formylmethyl) butane-1, 4-dicarbaldehyde
(C)Hexane-3-acetal-1, 6-dial (D) 3-(Formylmethyl) hexane-1, 6-dial

55 Which of the following is crotonic acid:

(A) CH2= CH–COOH (B) C6H5–CH=CH–COOH
(C) CH3–CH=CH–COOH (D) CH  COOH
||
CH  COOH

56 The IUPAC name of is:

(A) 2-Chlorocarbonyl ethylbenzoate (B) 2-Carboxyethyl benzoyl chloride

(C) Ethyl-2-(chlorocarbonyl)benzoate (D) Ethyl-1-(chlorocarbonyl)benzoate
O
||
57 The IUPAC name of C  CH 3 is:
(A)Phenyl ethanone (B) Methyl phenyl ketone
(C) Acetophenone (D) Phenyl methyl ketone

58 Structural formula of isopropyl methanoate is:

(A) CH  C  O  CH  CH (B) H  C  O  CH 2  CH  CH 3
3 3
|| | || |
O CH 3 O CH 3

(C) CH 3  C  O  CH 2  CH 2 (D) H  C  O  CH  CH 3
|| | || |
O CH 3 O CH 3

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 CH-11 NOMENCLATURE
59 Which of the following is not correctly matched:
(A) Lactic acid CH 3  CH  COOH
|
OH

(B) Tartaric acid HO  CH  COOH

|
HO  CH  COOH
(C) Pivaldehyde CH3C(CH3)2CHO

CH 3  CH  CH 2  CH 2  CH 2  CH 2  CH 3
(D) Iso-octane |
CH 3

EXERCISE - 2
MULTIPLE CHOICE(S) CORRECT TYPE QUESTIONS
1. Which of the following compound has wrong IUPAC name ?
(A) CH3 – CH2 – CH2 – COO – CH2CH3 Ethyl butanoate

(B) CH 3  CH  CH 2  CHO 3-Methylbutanal

|
CH 3
(C) CH 3  CH  CH  CH 3 2-Methyl-3-butanol
| |
OH CH 3
O
||
(D) CH 3  CH  C  CH 2  CH 3 2-Ethyl-3-pentanone
|
CH 3 H
|
2. The correct IUPAC name of the compound CH 3  CH 2  N  CH  O is
(A) N-formylaminoethane (B) N-ethylmethanamide
(C) N-ethylmethanamide (D) ethylaminomethanal
3. The compound which has one isopropyl group is :
(A) 2 , 2 , 3 , 3 - tetra methyl pentane (B) 2 - methyl butane
(C) 2 , 2 , 3 - trimethyl pentane (D) 2 , 3 - dimethyl pentane
4. The structure and IUPAC name of the acrylic acid is:
(A) CH2=CH–CH2–COOH (B) propenoic acid
(C) CH2=CH–COOH (D) Butenoic acid
5. Identify the wrongly named compound:
CH3 O
(A) CH3– CH–C–CH2 –CH2–OH 4-methyl-3-oxo-1-pentanol

(B) CH3–CH–—C—CH–CH3 2-ethoxy-4-methoxy-pentan-3one

OCH3 O OCH2CH3

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 CH-11 NOMENCLATURE

O
(C) Diethyl-1,4-dioxide
O

CH2–CHCH

(D) 1-propynyl benzene

EXERCISE - 3
MATRIX MATCH

1 Column - I Column - II

(A) (P) Phenanthrene

(B) (Q) Anthracene

(C) (R) Azulene

(D) (S) Napthalene

EXERCISE - 4
SUBJECTIVE TYPE QUESTIONS

Give the IUPAC names for each of the following : Q.4

Q.1
Q.5

Q.6

Q.2
Q.7

Q.3 Q.8

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 CH-11 NOMENCLATURE

Q.9 O2N OH Q.22

Q.10 Q.23

Q.24
Q.11

Q.25
Q.12

Q.26
Q.13

Q.14 Q.27

Q.15
Q.28

Q.16

Q.29
Q.17

Q.30
Q.18
Q.31

Q.19
Q.32

Q.20

Q.33

Q.21

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 CH-11 NOMENCLATURE

Q.46 =C=O
Q.34

Q.47

Q.35

Q.48

Q.36

Q.49
Q.37
O Cl
|| |
Q.50 CH 2  C  CH 2  CH  CH 3
Q.38

Q.39

Q.51
Q.40

Q.52
Q.41

Q.53
Q.42

Q.54
Q.43

Q.44 Q.55

Q.45

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 CH-11 NOMENCLATURE
ANSWER KEY

EXERCISE - 1

Q.1 B Q.2 B Q.3 D Q.4 C Q.5 C Q.6 D Q.7 C

Q.8 B Q.9 A Q.10 B Q.11 D Q.12 A Q.13 A Q.14 A
Q.15 B Q.16 D Q.17 C Q.18 B Q.19 C Q.20 D Q.21 B
Q.22 A Q.23 B Q.24 C Q.25 D Q.26 B Q.27 B Q.28 A
Q.29 C Q.30 D Q.31 D Q.32 C Q.33 B Q.34 B Q.35 B
Q.36 B Q.37 B Q.38 C Q.39 C Q.40 B Q.41 C Q.42 C
Q.43 C Q.44 C Q.45 A Q.46 D Q.47 B Q.48 D Q.49 B
Q.50 B Q.51 A Q.52 B Q.53 B Q.54 D Q.55 C Q.56 C
Q.57 A Q.58 D Q.59 D

EXERCISE - 2

1. C,D 2. B,C 3. B,D 4. B,C 5. ACD

EXERCISE - 3

1. (A) Q, (B) S , (C) P , (D) R

EXERCISE - 4

1 1 2 3 4 5
5 CH 2  C  CH 2  CH  CH 3
4 5 6 7 8
CH3  CH2  CH CH2  CH2  CH2  CH3 | |
| CH 3  CH  CH 3 CH 3
CH2  CH2  CH3 2-Isopropyl-4-methylpentene
4-Ethyl octane or 4-Methyl-2-(methyl ethyl) pentene

1 2 3
5 4
6 CH 2  CH  CH 2  OCH3
CH 3  CH  CH 3
3-Methoxypropene
3| 2 1
2 CH 3  CH 2  CH  CH  CH 3
| 4 3 2 1
CH 3 7 CH 2  CH  C  CH 2
|| |
3-Ethyl-2,4-dimethyl pentane O OH
1-Hydroxybut-3-en-2-one
3 5-Methyl hepta-1,3,6-triene
8 CH 3  CH  C  CH 2  OH
|
4 CH 3  CH 2 CH 2 CH 2  CH 3
| ||
C  C  CH 2-Ethylbut-2-en-1-ol
Hexen-3-yne

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 CH-11 NOMENCLATURE

3 2 1
9 CH  CH  CH 2 33 5-amino-6(1-methyl propyl) cyclo-hex-2-enol
| |
NO 2 OH 34 2-bromo-2-methyl cyclopentanone
3-nitroprop-2-en-1-ol
35 Methyl-2-methoxy-6-methyl-3- cyclohexene
OH O carboxylate
| ||
10 CH 2  CH  CH  C  C  CH
6 5 4 3 2 1 36 Bicylo(2.2.1)heptane
4-hydroxyhex-5-en-1-yn-3-one 37 9-methyl bicyclo(4.2.1) nonane
11 CH 3  C  CH 2  C  CH 3
|| || 38 spiro (2.5) octane
O O
39 spiro(4.5) decane
Pentane-2,4-dione
5 4 3 2
40 Bicyclo (1.1.0) butane
12 CH 3  CH 2  CH 2  CH  CHO
|
CN 41 Bicyclo(4.4.0) decane
1

2-Formyl pentane nitrile 42 Bicyclo(2.2.1) heptane

13 2,2,6,7-tetramethylocatane
43 8-chloro bicyclo(4.2.0) oct-2-ene
14 3-Ethyl-4,6-dimethyloctane
15 5 Methyl cyclohexa-1,3-diene 44 2-cyclopenten-1-ol
16 1,3-cyclobutadiene
17 1,2-epoxy propane 45 Ethyl-2-oxo-cyclo pentane carboxylate
18 1,3,4-trimethyl-1-cyclobutene 46 Cyclohexylidene methanone

19 Methylene cyclohexane 47 Bicyclo (3.1.0) hexane

20 1-ethyl-2-methylcyclopentane
48 Cyclohex-2-en-1,4-dione
21 1-methyl-3-(methyl ethyl cyclohexane)
or 3-isopropyl-1-methylcyclohexane 49 2-ethynyl cyclohexanol
22 Butyl cyclohexane
23 Isopropylidenecyclopentane 50 4-chloro-1-cyclopentyl pentane-2-one
or 1-methyl ethylidene cyclopentane
51 1-Amino methyl-2-ethyl cyclohexanol
24 Cyclopropanecarboxylic acid
25 Cyclopent-2-en-1-one 52 1-propyl-4-isopropyl-1-cyclohexene
26 1-(3-butenyl) cyclopentene or 4-(methyl ethyl)-1-propyl cyclohexene
27 1,2-diethenyl cyclohexene
53 2-(2-oxo-cyclohexyl) propanoic acid
28 1-cyclohexyl-1-propanone
29 Ethyl cyclohexanecarboxylate 54
30 4-Bromo-2-ethyl cyclopentanone 3-ethoxy-1(1-nitrocyclohexyl)-hex-4-en-1-one
31 3-(hydroxymethyl)-5-methylheptanal
55 1,3-diphenyl-1,4-pentadiene
32 2-Bromo-6-oxocyclohexanecarbaldehyde

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 CH-12 GENERAL ORGANIC CHEMISTRY

CHAPTER-12
GENERAL ORGANIC CHEMISTRY
A chemical equation is a symbolic representation of a chemical change. It indicates the initial
reactants and final products involved in a chemical change. Reactants generally consist of
two species:
(i) One which is being attacked; it is called a substrate.
(ii) Other which attacks the substrate; it is referred to as a reagent. These two interact to
form products.

Substrate + Reagent Products

It is important for us to know not only what happens in a chemical change but also known how
it happens. Most of the reactions are complexes and take place via intermediates which may
or may not be isolated. The intermediates are generally very reactive. They react readily with
other species present in the environment to form the final products. The detailed step by
step description of a chemical reaction is called its mechanism.
Substrate intermediates Products
Mechanism is only a hypothesis which explains various facts regarding a chemical change.
The reactions of organic compounds essentially involve changes in the existing covalent bonds
present in their molecules. These changes may involve electronic displacements in the bonds,
breaking of the bonds, energy changes accompanying the cleavage and formation of new
bonds. To understand clearly the mechanism of various organic reactions, it is thus essential
to have knowledge about the following well established concepts:
(i) Electronic displacements in bonds, (ii) Cleavage (fission or breaking) of covalent bonds,
(iii) Nature of attacking reagents.
1. Electron Displacement in Organic Molecules :
In organic molecules different reactions depend on the electron density in their molecules.
Since majority of attacking reagents are polar, i.e. nucleophilic (or) electrophilic, hence in organic
compounds permanent (or) temporary polarity is developed by temporary (or) permanent
electron displacements.
The different electronic effects which operates in covalent bonds are
(a) Inductive effect (b) Mesomeric and resonance effect
(c) Electromeric effect and (d) Hyper conjugation

(a) Inductive Effect

In a covalent single bond between unlike atoms, electron pair forming the bond is never
shared absolutely equally between the two atoms ; it tends to be attracted a little more towards
the more electronegative atom of the two. Thus in an alkyl chloride, electron density tends to
be greater nearer chlorine than carbon, as the former is the more electronegative; this is
generally represented as in

Cl Cl

If the carbon atom bonded to chlorine is itself attached to further carbon atoms, the effect can
be transmitted further . For example C2H5 – Cl.

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 CH-12 GENERAL ORGANIC CHEMISTRY

In ethyl chloride the effect of the chlorine atom, partial appropriation of the electrons of the
carbon chlorine bond is to leave C1 slightly electron deficient this it seeks to rectify by in turn,
appropriating slightly more than its share of the electrons of the bond joining it to C2, and so
on down the chain. The effect of C1 on C2 is less than the effect of Cl on C1. However it decreases
as the distance from source (more electronegative atom) increases. From practical point of
view, it may be neglected after third carbon atom.
Inductive effect is denoted by the symbol ‘I’ and represented by a straight arrow ( ), the
arrow head pointing towards the source.
The inductive effect causes certain degree of polarity in the bond which in term renders the
bond much more liable to be attached by other charged atoms (or) group.
The characteristic of inductive effect are :
(i) A permanent effect (ii) The electron never leave their original atomic orbital
(iii) Operates through bond (iv) Polarisation of electrons is always in single
direction.
(v) Its magnitude (i.e. electron with drawing or donating power) decreases with increase in
distance

Inductive effect is of two types

(1) Electron with drawing (–I effect)
(2) Electron releasing (+I effect)

Atoms (or) groups which attract electrons more strongly than hydrogen are called attracting
(or) withdrawing groups and produce –I effect. The following is the order of decreasing –I effect.
NR 3 , SR 2+ , NH 3+ , NO2, CN, SO3H, CHO, CO, COOH, COCl, COOR, CONH 2, OH, OR, F¯,
Cl, Br, I, NH2, C6H5, CH2 = CH2, H.

Atoms (or) groups which attract electrons less strongly than H are called as electron releasing
or repelling groups and produce +I effect. Following is the decreasing order of +I effect.
COO–, R3C, CHR2, CH3, H

Applications of Inductive Effect

(i) Dipole moment: Since, inductive effect leads to a dipolar character in the molecule, it develops
some dipole moment in the molecule, which increases with the increase in the inductive effect.
CH 3 I CH 3 Br CH 3 Cl
1.648D 1.79D 1.83D
Increasing dipole moment

(ii) In Bond Length: With increase in inductive effect, the bond length usually decreases because
of increased ionic character,
CH 3 F CH 3 Cl CH 3 Br CH 3 I
1.38Å 1.78Å 1.94Å 2.14Å
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 CH-12 GENERAL ORGANIC CHEMISTRY

(iii) Strength of Fatty Acids: As the number of alkyl groups attached to –COOH group increases,
the acid strength decreases. Thus formic acid is stronger acid than acetic acid which is stronger
than propionic acid and so on, due to increasing +I effect of alkyl groups.

O O H3C

H H3C O

O H O H O H
(Formic acid) (Acetic acid) (Propanoic acid)

(iv) Strength of Substituted Acids: Chlorinated acetic acids are stronger than acetic acid due to
the – I effect of chlorine atom.
O
O
H3 C Cl H
+I O
-I
O
H (mono chloro acetic acid)
(Acetic acid)
Larger the number of chlorine atoms, the greater will be –I and the stronger will be the acid.
Cl Cl

Cl COOH COOH Cl H3C COOH

Cl Cl COOH

The relative strength of the different halogen substituted acids is

FCH2COOH ClCH2COOH BrCH2COOH ICH2COOH

Key Concepts - 1

1 Which of the following does not represent the correct order of –I effect of the substituent?

(a) > >

(b) > > –NH2

(c) > –O–CH 3 > –O–H

(d) –OH > –C CH > –CH=CH 2

2 Arrange –NO2, –F, –COOH, –Cl and –C 6H5 in order of –I effect.
(a) –F > –NO2 > –COOH > –Cl > –C6H5
(b) –COOH > –NO2 > –F > –Cl > –C6H5
(c) –C6H5 > –Cl > –COOH > –NO 2 > –F
(d) –NO2 > –COOH > –F > –Cl > –C6H5

3 Correct order of – I effect is/are :

(a) – CN > (b) >

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(c) – O–Ph > –S–Ph (d) >

4 The group showing strongest –I effect is :

(a) – F (b) (c) (d)

5 The order of –I effect of orbitals is

(a) sp3 > sp 2 > sp (b) sp 2 > sp 3 > sp (c) sp > sp 2 > sp 3 (d) sp3 > sp > sp2

6 The arrangement of –O–Na+, –OH, –O– –CH3 when attached to benzene in order of
inductive effect is :

(a) – > –OH > –O – –CH3 (b) –OH > –O– –CH3 > –

(c) –O– –CH3 > – > –OH (d) –O– –CH3 > –OH > –

7 Which of the following statement is true ?

(a) Inductive effect is a permanent effect.
(b) Inductive effects travels through bonds
(c) –I effect decreases the charge intensity at carbanion
(d) –I effect in chlorobenzene is minimum at para position

8 The arrangement of (CH 3)3C , (CH2)2CH , CH3CH2 when attached to benzene or

an unsaturated group in increasing order of inductive effect is
(a) (CH3)3C– < (CH 3)2CH– < CH3CH2– (b) CH 3CH2– < (CH3)2CH– < (CH 3) 3C–
– – –
(c) (CH3)2CH < (CH3) 3C < CH3CH2 (d) (CH3)3C– < CH 3CH2– < (CH 3)2CH–

9 Which order is correct regarding the –I effect of the substitutents?

(a) –NR2 < –OR > –F (b) –NR2 > –OR > –F
(c) –NR2 < –OR < –F (d) –NR2 > –OR < –F

10 The group showning strongest – I effect is :

CH 3 O O
| || ||
( )
(a) – F (b) N CH 3 (c) NH C CH 3 (d) O C CH 3
|
CH 3

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Key Concepts - 2

1 Correct order of –I effect :

(a) –F < – CF3 (b) –C CH < – C N (c) – C N > – (d) >

2 Which of the following does not represent the correct order of –I effect of the
substituent?
(a) I – < Cl – < Br – < F– (b) RS – < R2N – < RO –
(c) R2O+ – > R3N+ – > R2S+ – (d) R2O+ – > RO – > C6H5O –

3 What is the correct order of –I effect of the following groups?

(a) F > Cl > Br > I (b) N+H3 > –C C–H>–CH=CH2>H
(c) –NO2 > –CN > CO2H > –OH (d) All

4 Which of the following order(s) is/are correct regarding the I effect of the substituents
?
(a) I < Cl < Br < F (b) R3 < R2 < F

(c) SR < O R < R2 (d) NH2 < NH CH3 < R3

5 Maximum I effect is exerted by :

(a) F (b) O CH3 (c) NH2 (d)

6 The negative charge intensity at carbon is minimum in which of the following :

(a) CCl (b) (CH3)2 CH (c) (d)

7 Separate +I and –I effect species among the following :

(a) – COOH (b) – NO2 (c) – NH2 (d) H3C–
(e) –S – R (f) (H3C)3C – (g) C6H5– (h) C6H11–
(i) – NO (j) –SO2 –NH2 (k) – C CH
8 Which functional group show more inductive effect among the following pairs :

(a) (b) – NH2 & – N H 3 (c) O H 2 & – N H3

(d) –SO2–OH & –COOH (e) –COOH & –COOR (f) O H2 & – F
9 Compare the – I effect of the following :
(a) N (CH 3 ) 3 & NO (b) NO & CN
2 2

(c) CH Cl , CH Cl2 & – CCl (d) F & CF

2 2 3 3

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(e) , , , &

10 Among of following pairs, which has greater +I effect:

(a) , –CH2 – (b) –CH2–CH2–CH2–CH3 , –CH2–

2. Resonance

The bonding of many compounds can be represented adequently by a single lewis

structures but in many other compounds, the molecule can be represented by two or
more structures that differ only in the arrangement of electrons. These compounds contain
one or more bonding orbitals that are not restricted to two atoms but spread over three or
more several atoms in the molecule. For these molecules two or more Lewis structures
(Called canonical forms) are drawn and the molecule is taken to be a weighted average of
them. This representation of a real structures as a weighted average of two or more
canonical forms is called resonance. The energy of the actual molecule is obviously less
than that of any one Lewis structure. The difference in energy between the actual molecule
and the Lewis structure of lowest energy is called resonance energy.

* Higher the resonance energy more will be the stability of the molecule.
Delocalisation of electrons
Resonance structure :
They are hypothetical structures which do not have any real existence of their own.
Resonance structures are useful because they allow us to describe molecules and ion for
which a single lewis structure is inadequate. Resonance structures are also called
canonicals which are connected by double headed arrows ( ). The real structure is the
combination of all the possible resonance structure.

Rules for writing resonance structure :

1. In writing resonance structures. The position of nuclei should remain same in all the
structures.

These are resonance structures as only electrons have been moved.

This is not a resonating structure as hydrogen atom has been moved.

2. All resonating structures must obey valency rules. We should not write structures having
five bonds at carbon. For example

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3. The total charge on each resonance structure must be same.
For example

4. The number of paired electrons getting delocalised remains same for all resonance
structures.
For example:
4 paired e– getting delocalised in both canonicals.

Also the number of unpaired electrons getting delocalised remains same in all resonance
structures.
This is not a cannonical structure.
5. The predicted stability of the actual molecule is more than the predicted stability of the
resonance structure. That means the energy of actual molecule is lower than the energy
of any contributing structure.

6. Equivalent resonance structures make equal contribution to the hybrid and a system
described by them has a large resonance stabilization.
For example:

Sodium acetate is more stable than acetic acid as it is highly resonance stabilized due to
the formation of two equivalent resonance contributors.

7. The more is the predicted stability of resonance structure, the greater is its contribution to
the resonance hybrid. The stability of canonicals (resonance structures) can be compared
by using following rules.
Canonicals in which all atoms have a complete octet are more stable and they
make a huge contribution to the resonance hybrid.

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Structure II makes a large stabilizing contribution to the hybrid as it has atoms with
a complete octet.

Canonicals with charge separation are unstable. It takes a lot of energy to separate
opposite charges hence structures in which opposite charges are separated have
greater energy (lower stability) as compared to those having no charge separation
For example:

The contribution of structure II to resonance hybrid is less than structure I.

Canonicals with negative charge on more electronegative atom are more stable
as compared to canonicals with negative charge on less or non electronegative
atoms.

Contribution of Resonating structures :

The contribution of an individual factors:
(i) Neutral species is more stable than the charged (or dipolar spices).
(ii) Species having complete octet is more stable than species having incomplete octet

(I) and (II) are resonating structure of acyl cation. (II) will be more sable than (I).
(iii) If all structure have formal charge, the most stable one is that in which the positive and
negative charges reside on the most electropositive and most electronegative atoms of the
species respectively.

(iv) Resonating structure with a greater number of covalent bonds is more stable.
(v) increase in charge separation decreases the stability of a resonating structure.

Hence stability of II and IV will be the same and both will be more stable than III. The order of
stability of resonating structures in decreasing order will be as follows :
I > II IV > III
Note : All the resonating structure do not contribute equally to the real molecule .
Their contribution is a direct function of their stability.

Resonance and Bond order :

Bond order in conjugated compound or bond order in compounds which exhibit resonance =
Total number of bonds on central atom
Number of resonating structures
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For example :

2 1
Bond order of carbon in benzene = = 1.5
2
Steric Inhibition of Resonance:
The most important condition for resonance to occur is that the involved atoms in resonating
structure must be coplanar or nearly coplanar for maximum resonance. If this condition does
not fulfill, the involved orbitals cannot be parallel to each other and as a consequence
delocalisation of electrons or positive charge cannot occur. The planarity of orbitals are inhibited
by the bulky groups present on adjacent atoms. This phenomenon is known as steric inhibition
of resonance. For example, in dimethyl aniline (I) the orbital having lone pair of electrons
present on nitrogen atom is in the plane of the benzene hence lone pair of electrons present on
nitrogen atom is in the plane of the benzene ring hence lone pair takes part in the delocalisation.

In N, N-dimethyl-2, 6-dinitroaniline (II) the (CH3)2 groups is out of the plane of the benzene
ring owing to the presence of the two bulky nitro groups and consequently the lone pair of
electrons on the (CH3)2 group cannot get delocalised through lone pair,
conjugation.

Thus bulky groups present at ortho position inhibit delocalisation of lone pair of electrons or
positive charge present on key atom of the molecule. Steric inhibition of resonance has profound
effect on:

(i) Physical properties

(ii) Acidity and Basicity and
(iii) Reactivity of organic compounds

In nitro-benzene (I) bond length between carbon-nitrogen (bond -a) is in between single and
double due to the resonance but in compound (II) bond length between carbon-nitrogen is only
of single bond due to the inhibition of resonance.

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3. Aromatic Character of Compouns

According to the Hückel rule, a compound will be aromatic if it fulfils following four conditions:
(i) Compound should be cyclic (ii) Compound should be planar
(iii) Compound should be conjugated
(a) Double bond, Single bond, Double bond
(b) Double bond, Single bond, electron pair
(c) Double bond, single bond, positive charge
(iv) Compound should have (4n + 2) conjugated or delocalised electrons where n is a
whole number n = 0 , 1 , 2 , 3 , ........ 4n

Structure No. of conjugated electrons

14

Anti-Aromatic compounds

According to Huckel rule, compound will be anti aromatic if it will fulfil the following four conditions:

(i) Compound should be cyclic

(ii) Compound should be planar
(iii) compound should be conjugated and
(iv) Compound should have (4n) conjugated or delocalised electrons where n is whole
number
n = 1, 2, 3, 4, 5, 6
n (4n)
Structure (4n)
4

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Exception : Although cyclooctatetraene has (4n) electrons even then it is not an anti aromatic.
Geometry of this compound is non planar

Cyclooctatetraene

Note: Aromatic compounds are diamagnetic in character whereas anti-aromatic compounds

are paramagnetic in character:

4. Mesomeric Effect

Mesomeric effect is defined as permanent effect of electron shifting which results into
the electron accumulation at one ene of the molecule and depletion of electrons at other
end of molecule. This effect mainly operates in conjugated system of double bond. Hence
this effect is also known as conjugate effect.

Types of mesomeric effect

(a) Positive mesomeric effect (+M effect): When the group donates electrons to the conjugated
system, it is said to show + M effect.
(b) Negative mesomeric effect (–M effect). When the group withdraws electrons from the
conjugated system it shows –M effect .
Example:

(i)

(ii)

(iii)

(iv)

(v)

Difference between inductive and mesomeric effect

* Inductive effects travels through sigma bonds whereas mesomeric effect travels through
bonds or lone pair.
* Inductive effect decreases with the increase in distance from the group. The effect
becomes negligible after third atom in the chain whereas mesomeric effect is distance
independent. It travels from one end to other end of the chain provided conjugation exists.
* Inductive effect causes slight displacement of electrons from its position whereas
mesomeric effect causes complete transfer of electron pair. Hence mesomeric effect is
domintaing over inductive effect.

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Key Concepts - 3

1 Identify the group which exert –I, –M & +M effect

(a) –NO2 (b) –NO (c) –SO2H (d) –C N
2 Identify the group which exert –I, –M, +M effect–

(a) –CH=CH2 (b) –C CH (c) (d) All of these

3 Which of the following is strong withdrawing group

(a) –F (b) (c) (d)

4 Group shown strongest +M effect

(a) –NH2 (b) (c) –NH–CH3 (d)

5 Which of the following is correct order of +M effect

(a) –NH2 > –OH (b) –OH >

(c) –O– –CH3 > –OH (d) –NH– –CH3 > NH2

6 Which of the following show both +M and –M effect

(a) –Cl (b) –CH=CH2 (c) –F (d)

7 Which of the following is showing greater + M effect

(a) F (b) Cl (c) Br (d) I

8 Which of the following group when attached to benzene ring show withdrawing effect

(a) –NR (b) (c) –C2H5 (d) –OCH3

9 What is the correct order of +R effect

(A) (B) – –O–R (C) –NH2 (D) –OH

(a) A > D > C > B (b) A > B > C > D (c) A > C > D > B (d) A > D > B > C

10 Which of the following is releasing group when in resonance

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(a) (b) (c) (d) –F

Key Concepts - 4

1 Which of the following groups can either donate (+ M effect) or withdraw (–M effect) a pair of
electrons in resonance depending upon situation :
(a) – NO2 (b) – NO (c) – CH = CH 2 (d) – CHO

(e) – NH2 (f) –Cl (g) – Ph (h)

(i) (j) (k) (l) – CONH2

(m) – (n) – BH2 (o) (p) – CONHCH3

(q) – OCOCH3 (r) – COOCH3 (s) – COOH (t) – COCl

(u) – CN (v) – O – CH2 – CH 3

2 Draw canonical structures of the following compounds:

(a) CH 2=CH–CH=CH–NH2 (b) HO–CH=CH–

(c) (d) Ph–CH=CH–C N

(e) (f)

3 Draw resonating structure of the following:-

(a) CH 2 CH C H 2 (b) (c) (d)

(e) (f) CH3 C C H C CH3 (g)

|| ||
O O
4 In acylium ion the structure R – C O is more stable than R - C = O.
5 Account for the fact that C2-C3 bond length in 1,3-butadiene is shorter than expected value ?
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6 Denote -electron transfer in the following cases :-

(a) CH3O–CH=CH2 (b) CH2=CH-CH2-NO2

(c) (d)

7 Draw resonating structure of the following:-

2
(a) CO 3 (b) CH 3 C NH 2 (c)
||
O

(d) NH2–CHO (e) CH3COOH (f) CH3COONa

(g) (h) (i)

(j) (k) R – CO – CH = CH2 (l) CH3O–CH=CH–

(m) CH3–O–CH=CH– (n) CH 2=CH–CH=O (o)

(p) (q) CH2 = C = O (r) (s)

8 In which of the following charge is not resonance stabilized, show by writing canonical
structures:

(a) (b) (c)

(d) (e) (f)

(g) (h) (i)

(j) (k) (l)

(m) (n) (o) (p)

9 In which of the following lone-pair indicated is involved in resonance :

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(a) (b) (c)

(d) (e) (f)

(g) (h)

(i) (j)

10 Identify more stable canonical structure in each of the following pairs :

(a)

(b) (c)

(d)

(e)

(f)

(g)

(h)

(i)

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Key Concepts - 5
1 Which of the following in each pair has higher resonance energy
I II
(a) CH3COOH and CH3 COONa
(b) CH2=CH–O and CH2=CH–OH

(c) and

(d) and

(e) and CH2=CH–CH=CH–CH=CH 2

(f) CO32– and HCOO –

(g) and CH2=CH–CH2–

(h) and CH2=CH–CH=CH2

(i) and CH2=CH –

(j) and

(k) and

(l) and

(m) and

(n) and

(o) and

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(p) and

(q) and

(r) and

(s) and

(t) CH2=CH–O–CH=CH2 and CH2=CH–NH–CH=CH2

(u) CH 2 CH N H and HN CH N H

(v) CH3COCl and CH 3COF

(w) CH2=CH–F and CH 2=CH–Br

(x) CH2=CH–OH and CH2=CH–CH=CH–OH

5. HYPERCONJUGATION

Unlike the usual delocalization which involves electrons, a different type called hyper conjugation
involves electrons. This another type of resonance (hyper conjugation) is often invoked to
account for the stabilizing and electron donating effect of an alkyl group. Hyper conjugation
involves delocalization of C—H sigma electrons into an adjacent pi system. Thus propene may
be described as a hybrid of structures I and II. In canonical forms which involve hyper conjugation
there is no bond between the carbon and hydrogen and therefore this effect has also been
called no bond resonance [sacrificial hyper conjugation, since in II, there is one less real bond].
Alternatively, the molecular description is that this effect arises from the overlap of orbitals in
the alkyl group with the system.

The evidence for hyper conjugation is that in propene e.g., the C—C single bond is slightly
shorter than in ethane. Thus it is reasoned that C—C single bond in propene acquires some
double bond character. Moreover the heat of hydrogenation of propene (30.1 Kcal/mol i.e., 126
kJ/mol) is less than that of ethene (32.8 kcal/mol i.e., 137 kJ/mol). In fact at present the evidence
is against hyper conjugation in the ground states of neutral molecules. Evidence is there to
show that hyper conjugation is indeed important and significantly accounts for the stability of
carbocations and free radicals.
H H
CH 2CH CH 2 CH 2 CH — CH 2
I II

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Sacrificial hyper conjugation

H

Hyperconjugation in an alkene: overlap

between and orbitals.

Thus in hyperconjugation in the ground state of neutral molecules, the canonical forms invoke
not only no-bond resonance but a charge separation as well which however not possessed by
the main form.

Effects of Hyperconjugation
1. Stability of Carbonium ions: The order of stability of carbonium ions is as follows
(CH3)3C+ (CH3)2CH+ CH3CH2+
above order of stability can be explained by hyper conjugation. In general greater the number of
hydrogen atoms attached to -carbon atoms, the more hyper conjugative forms can be written
and thus greater will be the stability of carbonium ions.
H
CH3
+
H C H
H3C C 3 carbonium ion
H3C C
CH3
CH3
(9 equivalent forms)

H
CH 3
+
H C H
H 3C C
2 carbonium ion
H3 C C
H
(6 equivalent forms) H
H
CH 3 +
H C H
H C
H C 1° carbonium
H
H
(3 equivalent forms)

2. Stability of free radicals: Stability of free radicals can also be explained as that of carbonium
ions.
(CH 3 )3 C (CH 3 ) 2 CH CH 3CH 2 CH 3

3. Bond lengths : The bond length in a molecule changes if there is hyper conjugation, e.g., in
3 2 1
propene C H 3 — C H C H 2 , the C1 — C2 bond length is found to be more than 1.34Å while
the C2 — C3 bond distance is less than 1.54 Å (C—C single bond length).

4. Dipole moment: since hyper conjugation causes the development of charges, it also affects the
dipole moment of the molecule.
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5. Orientation influence of methyl group : The o, p directing influence of the methyl group in methyl
benzenes is attributed partly to inductive and partly of hyper conjugation effect.
CH3

[ Orientation influence of the methyl group due to + I effect ]

The role of hyper conjugation in O , P directing influence of methyl group is evidence by the fact
that nitration of P-isopropyl toluene and p-tert-butyl toluene from the product in which —NO 2
group is introduced in the ortho position with respect to methyl group and not to isopropyl or t-
butyl group although the latter groups are more electron donating than methyl groups i.e. the
substitution takes place contrary to inductive effect. Actually this constitutes an example where
hyper conjugation overpowers inductive effect.
H H
H C H H C H

H C CH3 H3C C CH3

CH3 CH3
Reverse Hyperconjugation
The phenomenon a of hyperconjugation is also observed in the system given below:

where X = halogen
In such system the effect operates in the reverse direction . Hence the hyperconjugation in
such system is known as reverse hyperconjugation .

The meta directing influence and deactivating effect of CX 3 group for electrophilic aromatic
substitution reaction can be explained by this effect.
X X X
X–C–X X–C X X–C X

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6. CLEAVAGE OF COVALENT BOND

Organic reaction is a process in which breaking and formation of covalent bond/bonds take
place. In organic reaction, the main organic compound which is converted into a new compound
by breaking and formation of covalent bonds is known as the reactant or substrate and the
new compound formed is known as the product. The chemical species which causes the
change is called the reagent.

CH3 – CH2 – Br + CH3 – CH2 – OH +

Substrate or Reagent Product
Reactant
Breaking of covalent bond of the compound is known as bond fission. A bond can be broken
by two ways:

(a) Homolytic fission or Homolysis

In this fission, the covalent bond is broke in such a way that each resulting species gets its
own electron. This leads to the formation of odd electron species known as free radical.

The factor which favours homolysis is zero or a small difference in electronegativity

between A and B. Homolytic bond fission takes place in gaseous phase or in the presence
of non polar solvents (CCl4, CS2)

Condition for homolytic bond Fission : Homolysis takes place in the presence or peroxide.
UV light, heat ( 500ºC), electricity and free radical. The process is known as initiation of free
radical reaction.

(i) Peroxide
A: B Aº + Bº
(ii ) h
(iii )
(iv) Electricity
or
( v) Free radical

(i) Homolytic bond fission gives free radical as the reaction intermediate.
(ii) Reaction mechanism of the reaction is known as free radical or homolytic mechanism.

(b) Heterolytic Bond Fission or Heterolysis

In heterolysis, the covalent bond is broken in such a way that one species (i.e., less
electronegative) is deprived of its own electron, while the other species gains both the electrons.

Thus formation of opposite charged species takes place. In case of organic compounds, if
positive charge is present on the carbon then cation is termed as carbocation. If negative
charge is present on the carbon then anion is termed as carbanion. Carbocation and carbanion
are the reaction intermediates.
The factor which favours heterolysis is a greater difference of electronegativity between A and
B.
Thus
(1) Heterolytic bond fission gives carbocation or carbanion as reaction intermediate.
(2) Mechanism of the reaction in which heterolytic bond fission takes place is known as
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heterolytic mechanism or ionic mechanism.
(3) The energy required for heterolytic bond fission is always greater than that for homolytic
bond fission due to electrostatic force of attraction between ions,

(c) Reactive Intermediates

A great majority of organic reactions are multistep processes involving intermediates whose life
time are usually very short. An understanding of the structures and properties of these
intermediates which are normal covalent compounds, ions or radical’s is of paramount importance
to an understanding of organic reaction mechanisms. As we shall see in the energy profile
diagrams, intermediates possess sufficiently low energy to be formed under the reaction
conditions, but in most of the cases are not stable enough to permit isolation. This is especially
true of those intermediates in which carbon has fewer than four covalent bonds. A brief description
of some common kinds of intermediates is given below.

7. CARBOCATIONS

Carbocations are the key intermediates in several reactions and particularly in nucleophilic
substitution reactions.

Structure : Generally, in the carbocations the positively charged carbon atom is bonded to
three atoms and has no lone pairs on carbon. Carbon has six valence electrons. It is sp 2
hybridized with a planar structure and bond angles of about 120°.
R

Orbital picture of carbocation

There is a vacant unhybridized p orbital which e.g., in the case of C H3 lies perpendicular to the
sp2 hybridised plane..

Formation : Carbocations can be generated in a variety of way’s some of the reactions in

which carbocations are formed are summarized below.

1. Solvolyis of C—X bond (X = halogens, OBs, etc]

R —X R X–
2. Deamination of amines by nitrous acid.
HNO 2
R — NH 2 RN 2 R N2
3. Protonation of alcohols followed by dehydration
H
R — OH R O H2 R H2O

Stability: There is strong evidence, both physical and chemical, that alkyl groups are more
electron-donating than hydrogen. It , therefore, follows that when these groups are attached to
the electron-deficient carbon of the carbocation, they tend to release electrons and partially
compensate for the electron-deficiency of the positive carbon. The positive charge thus gets
dispersed over all the alkyl groups and this dispersal of charge increases the stability of the
whole system. Accordingly, tertiary carbocations are more stable than secondary ones which
in turn are stabler than primary carbocations.

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R H H H

R C R C R C H C

R R H H
The greater stability of alkyl substituted carbocations is sometimes partly ascribed to the
phenomenon of hyperconjugation. According to this, the electrons of an C—H bond can
be delocalized into the unfilled p orbital of the positive carbon atom, thus spreading the charge
over all such bonds. For an alkyl-substituted carbocation, several hyperconjugative resonance
forms can be written each having the same number of covalent bonds as the first structure.

H H H H

H C CH2 H C CH2 H C CH2 H C CH2

H H H H

In case of a secondary carbocation, more equivalent structures can be written than for a primary
carbocation whereas still greater number of such structures can be written for a tertiary
carbocation.
H H

H C H H C H
Five more eqivalent
H3C C H3C C structures

H H
H H

H C H H C H
Eight more eqivalent
H3C C H3C C structures

CH3 CH3
Resonance is an important factor that enhances the stability of a carbocation by delocalization
of its charge in systems like allyl and benzyl carbocations.

CH 2 CH2 CH2 CH2

Triphenyl carbocation is so stable that when triphenylmethyl bromide is placed in liquid sulphur
dioxide (a solvent with which carbocation does not react) it is possible to determine it quantitatively
by measuring the electrical conductivity of the solution.
C6 H5 C6 H 5
liquid SO 2
H 5C 6 C Br H 5 C6 C Br

C6 H5 C6 H 5

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CPh2 CPh2 CPh2

etc. CPh2
Steric effects also play key role in the ease of formation and stability of carbocations derived
from highly substituted substrates. The stability of such carbocations is attributed to the steric
relief. In substrates such as tri-isopropyl chloride, the three bulky isopropyl groups are pushed
together due to sp 3 angle of 109.5°. This pushing together results in a strain called B strain (or
back strain). When this ionizes, the angle expands from 109.5° ( sp 3 ) to 120° ( sp 2 ) resulting in
the relief of this strain due to increase in space between the alkyl groups.
CH3 H3C CH3
H3C HC CH
109.5°
Cl H3 C
H3C CH 109.5° 120°
CH3
CH HC
H3C CH33
H3C CH3
Such a carbocation would resist addition of a nucleophle as it would result in the crowding of
bulky groups together.

Key Concepts - 6

1 Relative stabilities of the following will be in the order -

(i) (ii) (iii) (iv)

(a) i < ii < iii < iv (b) iv < iii < ii < i (c) iv < ii < iii < i (d) ii < iv < iii < i

2 Most stable carbocation is

(a) (b) (c) (d)

3 Stability of carbocations is in the order

(i) (ii) (iii)

(iv) (v)
(a) iv > ii > i > v > iii (b) i > ii > iii > iv > v (c) iii > i > ii > v > iv (d) i > iv > ii > iii > v

4 The stability order of the following carbocation

I. II. III. IV..

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(a) IV > III > II > I (b) I > II > III > IV
(c) III > II > I > IV (d) II > I > III > IV

5 The most stable carbocation is:

(a) (b) (c) (d)

6 The most stable carbocation is :

(a) CH3 (b) (c) CH 3 OCH3 (d)

7 Which carbocation is the most stable:

(a) (b) (c) (d)

8 Which of the following is most stable:

(a) (b) (c) (d)

9 Most stable cation

(a) (b) (c) (d)

10 Which one of the most stabilised

(a) (b) (c) (d) CH3

Key Concepts - 7

1 The compound that give stable carbonium ions in acidic medium.

(a) 3-pentanol (b) 2 fluoro-3-pentanol
(c) 2, 2-difluoro-3 -pentanol (d) 1-fluoro-3-pentanol

2 The compound which gives the most stable carbonium ion on dehydration is
(a) (CH3)2 CHCH2OH (b) (CH3)3COH
(c) CH3CH2CH2CH2OH (d) CH3CH(OH)CH2CH3

3 In the acid catalyzed dehydration of neopentyl alcohol, the more stable carbonium ion formed is
–
(a) CH3–CH2–CH2–CH2– (b) (CH3)3 –CCH2+
(c)(CH3)2–CHCH2+ (d) (CH3)2– C CH2CH3
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4 Which among the following carbocations is most stable :

(a) (b) (c) (d)

5 The correct order of decreasing stability of the following carbocations is –

(a) I > II > III > IV (b) II > IV > III > I (c) III > IV > II > I (d) IV > I > II > III
6 Carbonium ion with highest stability :

(a) CD3 — (b) CD3 — (c) CD3 — (d) CH3 —

7 The most stable carbocation is :

( ) ( )
(a) CCl 3 C H2 (b) Cl C H CH3
( ) ( )
(c) Cl CH2 C H2 (d) F C H CH 3
8 In the following, the stability order of carbocation is :

(+)
I CH , II CH III CH OCH IV CH NH CH
2 3 3 3 3 3

(a) III > IV > II > I (b) IV > III > II > I
(c) IV > III > I > II (d) I > IV > III > II

9 Consider the following statements:

I. CH3O H2 is more stable than CH3 H2,

II. Me2 H is more stable than CH3CH2 H2,

III. CH2=CH– H2 is more stable than CH3CH2 H2.

IV CH2= is more stable than CH3 H2.

Of these statements:
(a) I and II are correct (b) III and IV are correct
(c) I, II and III are correct (d) II, III, and IV are correct.

10 Which of the following is most stable:

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(a) (b) (c) (d)

8. CARBANIONS

Carbanions are anions of carbon, generated by the removal of one of the groups attached to a
carbon without removing the bonding electrons. Thus, every carbanion possesses one unshared
pair of electrons and three pairs of bonding electrons around the central carbon atom which is
sp 3 hybridized.
R
R' C
R"
We know that the non-bonding electron pair repels the bonding pair more than the bonding
pairs repel each other and because of this, there is reduction of the angle between bonding
pairs to a value slightly lesser than the tetrahedral value of 109.5°. The configuration of simple
carbanions such as the methyl anion thus appears to be pyramidal just like that of ammonia
with which the methyl anion is isoelectronic. With this picture of carbanion, one can infer that if
the three substituents are different, the carboanion should be asymmetric and consequently
there should be retention of configuration in the reactions involving a carbanion intermediate.
However, it could not be demonstrated experimentally as the unshared pair and the central
carbon rapidly oscillate from one side of the plane to the other. This rapid equilibrium between
enantiomeric pyramidal structure thus explains the loss of optical activity associated with the
asymmetric carbanions.
R R H
R' C C R' H N
R" R" H

Formation : As there is little difference between the electro negativities of carbon and
hydrogen (2.5 and 2.1, respectively) the polarity of the C—H bond is very small. The heterolytic
fission of this covalent bond to form an anion and a proton should then be a very difficult
process. In other words, a hydrogen atom bound to an sp 3 carbon atom shows negligible
acidity. However, the presence of electron attracting substituents such as nitro, cyano or carbonyl
groups on the same carbon renders the hydrogen relatively acidic. The increase in acidity is not
only due to the electron-withdrawing ability of these substituents, but also due to their ability to
delocalize the negative charge of the anion. Thus hydrogens on the carbon atom alpha to nitro,
cyano or carbonyl groups have acidic character and can be removed as protons leaving
resonance stabilized anions.

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O O O
–H
H3C N H 2C N H2C N

O O O

O O O

H3C C H –H
H2C C H H2C C H

Carboanions are also formed when a nucleophile adds to a carbon-carbon double bond.
C 2 H5 OCH 2 — CH — C N
C2 H5 O CH 2 CH — C N
C2 H5 OCH 2 — C C N

Stability : As we have already seen, carbanions are stabilized by electron-withdrawing

substitutents. Generally speaking, a carbanion is stabilized by resonance if a double bond is
located to the anionic carbon. This explains the stability of the allylic and benzylic carbanions.

Ready conversion of triphenylmethane to the triphenylmethyl carbanion can be similarly explained.

Na
(C 6 H 5 )3 CH (C6 H 5 )3 C : Na

(C6H5)2 C (C6H5)2 C etc

The order of stability of the simple carbanions is : methyl > primary > secondary > tertiary

Another factor that contributes to the stability of carbanions is the extent of s-character of the
bonding orbitals of the carboanionic carbon. Carbanion stability, thus, has been found to be in
the order: RC C R 2 C CH R 3C — CH 2 . We have already seen that the carbon atom
in acetylene is sp hybridized (50% s character) and hence hydrogen atom attached to it should
be more acidic than that of ethylene where the carbon is sp 2 hybridized (33% s character).
An interesting example is cyclopentadiene which readily loses a proton to form the
cyclolpentadienyl anion.

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CH 3O –

H H
H H
The unusual stability of cyclopentadienyl anion is explained by the fact that although it has only
four electrons, two more electrons become available to it by the heterolysis of the C—H
bond thus forming a system of six electrons. These electrons are spread over all the five carbon
atoms like the delocalized aromatic system of benzene ring, thus conferring on it stability so
characteristic of the aromatic compounds.

Key Concepts - 8

1 Correct order of stability of following carbanions.

(I) (II) –CN (III) –NO2 is:

(a) I > II > III (b) III > II > I (c) I > III > II (d) III > I > II
2 The most stable carbanion among the following is

(a) (b) (c) (d)

3 Which one of the carbanions is most stable?

(a) (b) (c) (d)

4 Most stable carbanion

(a) (b) (c) (d)

5 What is the increasing order of stability: OH –, NH2–, H–C C– and CH3– CH2– .
(a) CH3–CH2– < NH2– < H–C C– < OH–. (b) H–C C– < CH3– CH2– < NH2– <OH–
(c) OH– < H–C C– < NH2– < CH3–CH2– (d) NH2– < H–C C– < OH– < CH3–CH2–

6 Most basic reagent of all :

( ) ( ) ( )
(a) CH 3 CH 2 (b) (c) CH 2 = CH (d) CH 3 CH CH3

7 Arrange the following carbanions in decreasing order of stability .

I CH2 = CH II. Ph III. Ph IV.

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(a) I > II > III > IV (b) I < II < III < IV
(c) III > IV > II > I (d) IV > III > II > I
8 Stability order:

I. II. III. IV.

(a) III > II > IV > I (b) III > II > I > IV (c) III > I > IV > II (d) III > IV > I > II

9. FREE RADICALS
There are two possible structures for simple alkyl radicals. Either a free radical may be a planar
species (A) in which the carbon atom bearing the odd electron in sp 2 hybridized (as in
carbocations) and the odd electron remains in the p-orbital, or it could have a shape resembling
a shallow pyramid (B) which is neither planar nor tetrahedral and the orbital containing unpaired
electron is some sort of a hybrid between a p and an sp 3 orbital.

The question as to whether free radicals exist in a planar configuration or in a rapid equilibrium
between the two pyramidal forms (B) is difficult to answer with certainty. However, available
evidence indicates that the unpaired electron is in a p orbital. Resonance stabilized free radicals
certainly exist in planar configuration.
Homolytic cleavage
It is due to symmetrical breaking of covalent bond. Both the atoms are parted away by taking
equal number of electron

This type of cleavage requires high amount of energy either in the form of heat or light
Characteristics:
• Netural species
• Highly energized species i.e. quite unstable i.e. highly reactive. So the free radicals can go for
dimerisation or disproportionation
• Since free radicals are having unpaired electron hence paramagnetic as well as electron deficient
species. All the carbon radicals possess 7 e– i.e. requires one more electrons to complete its
octet. In other words we can say electron releasing groups stabilizes free radical whereas
electron withdrawing groups(EWG) destabilizes free radicals.

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Stability order:

• The higher the stability of the free radical, the faster it will be formed. In other words the smaller
the amount of energy required for bond breaking, the more stable is the radical. The following
example can be taken to justify the above statement.

a is vinylic H hence generates vinyl free radical.

b is allylic H hence will generate allyl free radical
c is 2ºH so 2º free radical
we know
Allyl radical > 2º > vinyl radical
Higher the stablity, the faster it will be formed i.e. requires least energy to break C–H bond.
Hence in decreasing order of dissociation enrgy

a c b
Example

If equivalent amount of toluene and cyclohexane treated with Cl2

in U.V. rays.
Solution

Toluene gives whereas cyclohexane gives (2º free radical). We know that benzyl

radical is more stable hence it will be quickly formed compared to 2º radical hence the major

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product will be .

• Free radical reaction is very much common is gaseous phase, Alkanes, some reactions of
alkenes and in nonpolar solvents.
• In the gas phase, formation of free radical is always less energy demanding than hetrolytic
fission. Radicals formed in the solution (i.e. non-polar solvents) are generally found to be less
slective in their attack on other species or on alternative position within in the same species
than carbocation or carbanion.
• Free radicals can be generated either by photolysis or thermolysis or redox reaction.
Photolysis:

(i) Me– –Me Me + –Me CO + Me•

2Me

(ii) (alkyl hypochlorite) RO + Cl

(iii)

Some times, the formation of radicals is facilated by simultaneous release of a very stable
molecule such as nitrogen.

(iv)

Thermolysis:
(1) Peroxides or peracid has a O–O bond strength of only 36 Kcal/mole and so it undergoes breaking
even at room temperature.

(ii)

(iii)

NB:– Photolysis is better method than thermolysis because energy can be transfered
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to a particular point i.e. more specific.
REDOX REACTOINS
One electron oxidation-reduction reactions are very often employed to produced radicals for
this purpose metal ions such as Fe2+/Fe3+ and Cu+/Cu++ are very frequently used:

(i)

(ii) Kolbe’s electrolysis is also the example of redox reaction (anodic oxidation of carboxylate ion)

(iii) Fenton’s reagent is also redox-reaction

–
Fe++ + H2O2 Fe+++ + OH + H
Hydroxyl radical produced can be used in oxidising organic substances such as

(iv) Electrolysis of ketones, results in their cathadic reduciton to radical anions, which dimerise to
form the dianions of pinacols

radical anions can also be formed by treating ketone with Na or Mg in non-polar solvents

• Free radical reaction is a chain reaction and proceeds through three steps

Key Concepts - 9

1 Stability order of the following is in the order

(I) (II) (III) (IV)

(a) IV < II < III < I (b) IV < II < I < III
(c) I < II < III < IV (d) IV < I < III < II

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2 Bond energy of C - H bonds :

(a) B > C > A (b) C > A > B (c) A > C > B (d) B > A > C

3 Which one is most stable free radical

(a) CH 2 CH (b) (c) (d) CH 2 CH C H 2

4 Most stable free radical is:

(a) (b) (c) (d)

5 Which statement is correct for CH3– :

(a) It is paramagnetic in character (b) It is a neutral electrophile
(c) Formation takes place by homolytic bond fission (d) All are correct

6 The most stable free radical among the following is

(a) C 6 H 5 CH 2 C H 2 (b) C 6 H 5 C HCH 3 (c) CH 3 C H 2 (d) CH 3 C HCH 3

7 The relative stability of:

(i) (ii) (iii)

(a) i > ii > iii (b) i > iii > ii (c) ii > i > iii (d) iii > ii > i

8 Arrange the following in increasing order of stability of radicals

(I) (II) (III) (IV)

(a) II > I > IV > III (b) II > IV > III >I (c) II > III > I > IV (d) III > II > I > IV

10. CARBENES

Carbenes can be defined as neutral, divalent carbon intermediates in which a carbon is covalently
bonded to two atoms and has two non-bonding orbitals containing two electrons between them.
Theoretical considerations suggest that there are two possible kinds of carbenes, singlet and
triplet carbenes. In the singlet state, a carbon atom is presumed to approximate sp2 hybridization.

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Two of the three sp2 hybrid orbitals are utilized in forming two covalent bonds whereas the third
hybrid orbital contains the unshared pair of electrons. The unhybridized p orbital remains vacant.
Thus singlet carbene (A) resembles a carbocation very closely. On the other hand, carbon
atom of a triplet carbene (B) is sp hybridized and it is a linear or near-linear species. These two
hybrid orbitals are involved in the bond formation with two groups and the two electrons are
placed one each, in the equivalent, mutually perpendicular py and pz orbitals . Since these
electrons have parallel spins, a carbene with this structure is said to be in a triplet state.

(A) (B)

At first sight, it appears that a singlet carbene has lower energy as the unshared electron pair is
in a sp2 hybrid orbital ; but the considerations of the electron repulsion energy that must be
overcome to pair two electrons in a single orbital places it at the higher energy level than a triplet
structure. It is, therefore, reasonable to believe that the triplet state of a carbene is more stable
than the singlet state and should be expected to be the ground state.
Formation : Photochemical or thermal cleavage of cyclopropanes and oxiranes is a common
method for the generation of carbenes.
H5C6 CH2
hv
C CH2 or
H 2C C6 H 5CH CH 2
H

H 5 C6 O O
hv
C CH C6 H 5 HC HC — C 6 H 5
H C6H5

Stability: Carbenes in which the carbene carbon is attached to two atoms, each bearing an
unshared pair of electrons, are somewhat more stable due to resonance.
R2 N R2 N R2N
C C C
R2 N R2 N R2N
Nitrenes
, Nitrenes are electron-deficient monovalent nitrogen species in which the nitrogen atom has a
sextet of electrons in its outer shell. There are two possible forms in which a nitrene can exist,
the singlet and triplet states.

R—N R—N
singlet triplet
Arynes
Arynes may be defined as aromatic compounds containing a formal carbon-carbon triple bond.
The best known aryne is benzyne which may be regarded as the aromatic counterpart of acetylene
or in other words, it is benzene minus two ortho hydrogens and can also be called as
dehydrobenzene.

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The benzyne bond is not like the triple bond of acetylene where the two carbons form a bond
using sp orbitals and the remaining p orbitals are used to form bonds. Such a structure is not
possible in benzyne because of the hexagonal geometry associated with the benzene ring.
Most probably the new bond of benzyne is formed by the overlap of sp2 orbitals belonging to
two neighbouring carbon atoms. These sp2 orbitals are orthogonal to the molecular orbital of
the benzene ring.

Formation: Benzyne has been shown to be intermediate in several important organic reactions.
For example, in the presence of a strong base, aryl halides eliminate HX from 1, 2-positions to
produce benzyne which then rapidly reacts with the available nucleophile to regenerate the
aromatic system.
Br
NH 2 NH 3 Br
H

NH 3 NH2
NH 3

Stability: The new bond of benzyne, formed by the overlap of sp 2 orbitals belonging to two
neighbouring carbon atoms in unstable, and therefore benzynes are extremely reactive chemical
species.

Key Concepts - 10

1 Arrange the following in increasing order of stability

(I) H2 (II) CH3– H (III) CH3– –CH3

2 Arrange the following in decreasing order of stability

(I) H2 (II) CH3– H (III)

3 Arrange the following in increasing order of stability

(I) :CF2 (II) :CCl2 (III) :CBr2 (IV) :CI2

4 Which of the following reaction generate carbene:

h
(a) CHCl3 + (b) CH2N2
Zn
(c) CH2I2 (d) All of these

5 The carbene formed in the following reaction is:

CHClBrF + ?

(a) :CHF (b) :CClF (c) :CFBr (d) :CClBr

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6 Which of the following reaction involve carbene intemediate:

(a) CH3–HC=CH–CH3 + CHClF2

(b) + CHCl3 (c) R–NH2 + CHCl3 R–N C

(d) All of these

11. ACID AND BASED

Bronsted lowry defination of acid and bases

ACID : Substance that can donote or loose a proton. When acid looses its proton, the
molecule or ion formed is called conjugate base of that acid. More is the stability of conjugate
base, more is the acidic nature of acid.
H–Cl H + Cl
The chloride ion is the conjugate base of HCl
Example

Acidic Nature of acid is directly proportional to the stability of conjugate base

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BASE : Substance that can accept a proton. The molecule or ion that forms when a base
accepts a proton is called the conjugate acid of that base.

Lewis definition of acids and base

ACIDS : Electron pair acceptors
BASE : Electron pair donors. Ease of donotion of lone pair is basicity. If the lone pair is
involved in resonance, tendency to donate lone pair decrease, hence basic nature
decreases.

Acidity of phenol
The acidity of phenol is due to the + M effect of OH group. The mesomeric transfer of the lone
pair on the oxygen atom of phenol to the electrons of the benzene ring results in several
resonance structures with positive charge on the oxygen atom. This aids the hydrogen atom
of OH group will leave as proton.

The ionization is specially aided due to the formation of the relatively more stable phenoxide ion.
The charge delocalization in phenoxide ion affords greater stability over phenol in which charge
separation occurs in the canonical forms.
O O O O

Hence , phenol prefers to ionize, i.e. it is acidic .

Acidity of -Hydrogens
-Hydrogen of carbonyl compounds , nitrites , acids , nitro compounds are acidic in character .
In other words we can say that
(i) -Hydrogens are acidic in character when –I group is present on the -carbon.
(ii) Acidity of -hydrogens depends on the stability of carbanion which is obtained by the
ionisation of the compound

Thus acidity depends on the stability of .

Stability of anion depends on two factors.:
(a) Stability of carbanion –I power of the group present on -carbon

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For example;

(b) Stability of carbanion number of resonating structures.

Thus -hydrogen of nitro methane is acidic due to inductive effect as well as delocalisation of
negative charge.
Key Concepts - 11

1 Identify the acids and bases in these reactions :

(A) (B)

(C) (D)

(E)

(F)

2 Write the conjugated bases of the following :

(a) CH3–CH=CH2 (b) CH 3 C CH

(c) CH3–CH2–CH3 (d)

O
||
(e) (f) CH 3 C H

(g) CH 3 C O CH 2 CH 3 (h)
||
O

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(i) (j)

O
||
(k) CH 3 C NH 2 (l) Br-CH2-CH2-Cl

(m) CH3– –CH2– –O–CH2–CH3 (n) CH 3 C CH 2 C CH 3

|| ||
O O

(o) Caro’s acid (p)

(q) HO–CH2–CH2–SH (r)

3 Write the conjugated Acid.

(a) acetic acid (b) acetone
NH 2
|
(c) CH 3 NH C NH (d) propene
(e) ethyl acetyl acetate (f) propyne
(g) ethyl acetate (h) acetamide
(i) CH 2 CH C CH (j) HO CH 2 CH 2 SH
(k) CH2=CH–CH2–C CH

(l) . (m)

H
N
(n) (o)
N
H

(p) (q)

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(r) (s)

(t) (u)

(v)

Key Concepts - 12

1 From the following reactions :

HC CH + LiNH2 NH3 + HC CLi and H2O + HC CLi H — C C — H + LiOH.
Predict which of the following facts regarding the basic strength is correct.
(a) Li NH2 > HC C Li > LiOH (b) Li NH2 > LiOH > HC CLi
(c) HC C Li > LiNH2 > LiOH (d) HC C Li > LiOH > LiNH2

2 Among the following the strongest base is :

(a) C6 H5 NH2 (b) p NO2 C6 H4 NH 2
(c) m NO 2 C6 H4 NH2 (d) C6 H5 CH2 NH2

3 Sodium phenoxide (C6H5ONa) is a stronger base than:

(a) CH3CH2ONa (b) NaNH2 (c) C6H5Li (d)

4 Which of the following is strongest base?

(a) (b) (c) (d)

5 Among the following compounds, the strongest base is:

(a) NH2– –NH2 (b) NH2– NH2 (c) C6H5–NH2 (d) CH3–NH–CH3

6 Which one of the following is most basic:

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(a) (b) (c) (d)

7 Weakest base among the following is:

(a) (b) (c) (d)

8 Which of the following is the strongest base:

(a) (b) (c) (d)

9 Strongest base among the following is:

(a) (b) (c) (CH3)3N: (d)

10 Which is the most basic among following pairs of compounds:

(a) (b)

(c)

(a) a-I, b-II, c-I (b) a-I, b-I, c-I (c) a-II, b-I, C-II(d) a-II, b-II, c-II

Key Concepts - 13

1 In the following compounds:

I. II. III. IV.

the order of acidity is:

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(a) IV < I < III < II (b) III < I < IV < II (c) II < I < III < IV (d) I < III < II < IV

2 The position of equilibrium lies to the right in each of these reactions

N2H5+ + NH3 NH4+ + N2H4
NH3 + HBr NH4+ + Br–
N2H4 + HBr N2H5+ + Br–
Based on this informmation. What is order of acid strength.
(a) N2H5+ > N2H4 > NH4+ (b) N2H5+ > HBr > NH4+
–
(c) NH3 > N2H4 > Br (d) HBr > N2H5+ > NH4+

3 Given below are three acids . The order of their acidic nature is : :
3

I. II. III.
3

(a) I > III > II (b) I > II > III (c) III > I > II (d) II > III > I
4 Among acetic acid, phenol and n-hexanol, which of the compound(s) will react with NaHCO 3
solution to give sodium salt and CO 2.
(a) acetic acid and phenol (b) acetic acid
(c) phenol (d) n-hexanol

5 Rank the following molecules in the order of increasing pK a

(I) (II) (III) (IV)

(a) II < III < I < IV (b) III < II < I < IV (c) I < IV < II < III (d) IV < I < III < II

6 Which of the following compound would be most acidic

(a) (b) (c) (d)

7 The correct order of acidic strength of following will be

(1) HCOOH (2) o-NO2C6H4COOH, (3) PhCOOH (4) p-NO2C6H4COOH
(a) 1 > 2 > 3 > 4 (b) 1 > 2 > 4 > 3 (c) 2 > 4 > 1 > 3 (d) 2 > 4 > 3 > 1

8 The decreasing order acidity of the following:

(I) (II) (III) (IV)

(a) I < II < III < IV (b) IV > III < II < I (c) III < IV < II < I (d) I < II < IV < III

9 Which of the following is most acidic?

(a) H 2O (b) CH3–CH2–OH (c) HO–CH2–CH2–OH (d) CH3O–CH 2–CH2–OH

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10 Arrange in acidic order .

I CH 3OH II CH 3SH III IV

(a) III > II > I > IV (b) IV > III > II > I (c) III > IV > II > I (d) IV > II > III > I

12. (A) NATURE OF ATTACKING REAGENTS

Organic reagents can be classified in two categories:
Electrophile : Electron deficient species or electron acceptor to form a covalent bond is
electrophile.
Nucleophile : Electron rich species or electron donor to form a covalent bond is nucleophile.

(a) Electrophiles
It can be classified into two categories:
(A) Charged electrophiles (B) Neutral electrophiles
(A) Charged electrophiles : Positively charged species in which central atoms has
incomplete octet is charged electrophile.

H , X , R , , ,

Note : All cations are charged electrophiles except cations of I A , II A group elements
,
Al+++ and
(B) Neutral electrophiles : It can be classified into three categories:
(I B) Neutral covalent compound in which central atom has incomplete octet is neutral
electrophile.
BeCl2, BH3, ZnCl2, AlX3, FeX3, ,
(II B) Neutral covalent compound in which central atom has complete or expended octet and
central atom has unfilled-d-sub-shell is neutral electrophile
SnCl4, SiCl4, PCl5, SF6, IF7
(III B) Neutral covalent compound in which central atom is bonded only with two or more than
two electronegative atoms is neutral electrophile.
BeCl2, BX3, AlX3, FeX3, SnCl4, PCl3
PCl5, NF3, , CO2, SO3, CS2, CX4
Note : (i) Cl2, Br2 and I2 also behave as neutral electrophiles.
(ii) Electrophiles are Lewis acids.

(b) Nucleophiles
Nucleophiles can be classified into three categories:
(A) Charged nucleophiles: Negatively charged species are charged nucleophiles.

(B) Neutral nucleophiles: It can be classified into two categories:

(I B) Neutral covalent compound, in which central atom has complete octet, has at least one

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lone pair of electrons an all atoms present on central atom should not electronegative, is neutral
nucleophile.
(nitrogen nucleophile)

H– –H, R– –H, R– –R (Oxygen nucleophiles)

H– –H, R– –H, R– –R (Sulphur nucleophiles

(Phosphorus nucleophiles)
(II B) Organic compound containing carbon, carbon multiple bond/bonds behaves as
nucleophile.
Alkenes, Alkynes, Benzene, CH2=CH–CH=CH2, CH2=CH–C CH

(C) Ambident nucleophiles: Species having two nucleopilic centres, one is neutral
(complete octet and has at least one lone pair of electrons) and other is charged (negative
charge) behaves as ambident nucleophile

Note : (1) Organometallic compounds are nucleophiles.

(2) Nucleophiles are lewis bases.

Organic compounds which behave as electrophile as well as nucleophile: Organic

compound in which carbon is bonded with electronegative atom (O, N, S) by multiple bond/
bonds behaves as electrophile as well as nucleophile.

, , , ,

, , ,

Note : During the course of chemical reaction electrophile reacts with nucleophile.

Key Concepts - 14 (a)

1 The nucleophilicity of:

(i) H2O (ii) HO– (iii) HS–
(a) i > ii > iii (b) i > iii > ii (c) ii > i > iii (c) ii > iii > i
(e) iii > ii > i

2 Which of the following is strongest nucleophile ?

(a) (b) (c) (d)

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3 Which of the following behave(s) both as a nucleophile and electrophile ?

(+)
(a) H O (b) CH C N (c) CH NH (d) H O
3 3 3 2 2

(–)
4 The reactivity of X is found lowest in :
(a) DMF (b) H2O (c) benzene (d) CH3OH

5 Which of the following is not an electrophile?

(a) (b) Br2 (c) (d) BH3

6 Which is most reactive electrophile

(a) (b) O 2N

(c) (d)

7 Which of the following is/are nucleophiles ?

(a) H O (b) Cl+ (c) BF (d) SH¯
2 3

8 The correct order of true/false statement is

(1) has electrophilic ‘N’ atom (2) is a nucleophile

(3) is an electrophile (4) SO 3 is an electrophile

(a) TTFF (b) TFTF (c) TFFT (d) FTTT

9 Arrange the following in decreasing order of nucleophilicity in aqueous medium.

Phenoxide ion Methonol CH3S– OH–
I II III IV
(a) III > IV > I > II (b) II > IV > III > I (c) IV > I > II > III (d) III > II > IV > I

10 Which of the following is weakest nucleophile:

(a) NH2–Cl (b) NH 2–OH (c) NH 2–NH2 (d) NH2–OCH 3

12. (B) LEAVING GROUPS :

Nucleophilic substitution reactions generally expressed as:
Nu¯ + R — L —Nu + L¯
where Nu¯ Nucleophile
R—L substrate
L Leaving group
The best leaving groups are those that become the most stable ions after they depart. Since
most leaving groups leave as a negative ion, the best leaving groups are those ions that stabilize
a negative charge most effectively. A good leaving group should be

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(i) electron-withdrawing to polarize the carbon atom
(ii) stable once it has left (not a strong base)
Key Concepts - 14 (b)
1 Rate of the reaction

+ Nu– + Z– is fastest when Z is

(a) Cl (b) NH2 (c) OC2H5 (d) OCOCH3

2 Leaving tendency of the following in increasing order will be :

( ) ( )
Cl CH COO
3
I II III IV
(a) II > I > IV > III (b) I > II > IV > III (c) III > I > II > IV (d) III > II > I > IV

3 The order of nucleofugality of the following reagent :

(i) (ii) Cl (iii) CF3– (iv) F–

(a) i > ii > iii > iv (b) iv > iii > i > ii (c) iv > iii > ii > i (d) iii> iv > ii > i

4 Which carbon atoms are most susceptible to nucleophilic attack?

(a) i and ii (b) ii and iii (c) ii and iv (d) i and iv

5 In the following groups :

– O CO CH3 (I) – O CH3 (II) –O –SO 2–CH3 (III) –O–SO2 CF3 (IV) –I (v)
the order of leaving group ability is :
(A) I > II > III > IV > V (B) IV > III > V > I > II
(C) III > II > I > IV > V (D) II > III > IV > I > V

6 Leaving tendency of the following in decreasing order will be :

( )
Cl ( )
CH 3COO( ) OH

I II III IV

(A) II > I > IV > III (B) I > III > II > IV (C) III > I > II > IV (D) III > II > I > IV

7 The leaving group ability for the indicated group (LG):

i ii iii
(a) i > ii > iii (b) i > iii > ii (c) ii < i < iii (d) ii > iii > i
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8 In which of the following reactions methanol is formed on treament with NaOH solution

(A) 3 (B) 3

CH3

(C) (D) CH –N–CH I

CH3

9. Among the following which is feasible ?

(A) R–O–R + HI RI + ROH
(B) X¯ + CH3–OH CH3–X +
Protic solvent
(C) KF + CH3–CH2–I CH3–CH2–F + I–
(D) R–NH2 + OH¯ R–OH + NH2¯

10. Among the following which is false statement ?

(A) The weaker the base after the group departs, the better the leaving group.
(B) A weak leaving group drives the equilibrium towards the reactants.
(C) Relative leaving group ability may vary with change of solvent.
(D) Better leaving group only increases S N2 rate, not SN1

11. (I) CH3Br (II) CH3F (III) CH3OH (IV) CH3OSO2CF3

The correct order of reactivity of above compounds towards CH 3O¯ in an SN2 reaction is :
(A) I > IV > II > III (B) IV > I > II > III
(C) IV > I > III > II (D) IV > II > I > III

12. (I) F–SO3 (II) CF3–SO3 (III) (IV)

The correct order of dcreasing leaving group capability is :

(A) II > I > IV > III (B) I > II > IV > III
(C) II > I > III > IV (D) I > II > III > IV

13. TYPE OF ORGANIC REACTIONS

The reactions of organic ompounds can be clasified into four main types:
(i) Substitution or displacement reactions (ii) Addition reactions
(iii) Elimination reactions (iv) Rearrangement reactions

(i) Substitution or displacement reactions:

Substitution or displacement reactions are those reactions in which an atom or group of
atoms attached to a carbon atom in a substrate molecule is replaced by another atom or group
of atoms. During the reation no change ocurs in the carbon skeleton, i.e., no change in the
saturation or unsaturation of the intial organic compound.
Depending on the mechanism, the substitution reactions are further classified into three types:

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(a) Free radical substituting reactions (b) Electrophilic substituting reactions

(c) Nucleophilic substituting reactions
Some of the example of substitution reactions are :
UV
(a) CH4 + Cl2 CH3Cl + HCl
light
methane
(Hydrogen atom is replaced by chlorine)

(b) CH3OH + HBr CH3Br + H2O

Methyl alcohol Methyl bromide

(c) C6H6 + HNO3 C6H5NO2 + H2O

Benzene (conc.) Nitrobenzene
(Hydrogen is replaced by NO2 group)

(d) C6H6 + C12 C6H5Cl + HCl

Benzene Chlorobenzene
(Hydrogen is replaced by chlorine)

(ii) Addition reactions :

Addition reactions are those in which the attacking reagent adds upto the substrate molecule
without elimination. Such reactions are given by those compounds which possess double or
triple bonds. In the process a triple bond may be converted into double bond or single bonds
and a double bond is converted into single bond. For each -bond of the molecule two sigma
bonds are formed and the hybridisation state of carbon atoms changes from sp and sp2 and
sp2 to sp3 .
Like substitution reactions, addition reaction are also of three type:
(a) Free radical addition reactions. (b) Nucleophilic addition reactions
(c) Electrophilic addition reactions.

Some of the examples of addition reactions are:

(i)

(ii) CH2=CH2 + Br2 CH2Br–CH2Br

Ethylene 1,2-Dibromoethane
(Ethylene bromide)

(iii)

(iv) CH3C N + H2O CH3– –NH2

Methyl cyanide Acetamide

(v) CH CH + HBr CH2=CHBr CH3CHBr2

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Acetylene Vinyl bromide 1,1-Dibromoethane
(Ethylidine bromide)
(iii) Elimination reactions
The reverse of addtion reactions are termed as elimination reactions. In these reactions generally
atoms or groups from two adjacent carbon atoms in the sybstrate molecule are revomed and
multiple bond is formed. In the process two sigma bonds are lost and a new -bond is formed,
i.e., state of hybridization of carbon atom changes from sp 3 and sp2 to sp.
Some example are :

(i)

(ii)

(iii)

(iv) Rearrangement reactions:

The reaction which involve the migration of an atom or group from one site to another within the
molecule (nothing is added from outside and nothing is eliminated) resulting in a new molecular
structure are known as rearrangement reactions. The new compound is actually the structural
isomer of the original one.
Some of the examples are :

(i)

(ii)

(iii) NH4CNO NH2–CO–NH2

Ammonium cyanate Urea

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O
OCCH3 OH OH
anhy.AlCl3 COCH3
(iv)
[Fries
rearrangement] COCH3
Phenylacetate
(ester)
– and -hydroxy acetophenone

Key Concepts - 15

1 The compound

(a) forms an addition compound with Br 2 (b) forms an addition product with HCN
(c) can be reduced to a secondary alcohol (d) is optically inactive

2 The order of reactivity towards nucleophilic substitution is :

I II III IV
(a) I > II > III > IV (b) IV > III > I > II (c) III > II > I > IV (d) II > I > IV > III

3 SN1 reaction is fastest in –

CH 3
|
(a) CH3CH2Cl (b) (c) CH 3 C Cl (d) CH 3 CH Cl
| |
CH 3 CH 2
|
CH 3
4 Towards electrophilic substitution, the most reactive will be
(a) nitrobenzene (b) aniline (c) aniline hydrochloride (d) N-acetylaniline

5 The more reactive electrophile obtained from the following acid chlorides when acetylated
with benzene is :

(a) (b)

(c) (d)

6 Which of the following requires radical intermediate ?

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(a) CH3 – CH = CH2 + HBr

(b) CH3 – CHO + HCN

(c) CH3 – CH = CH2 + HBr/H2O2 CH3 – CH2 – CH2 – Br

(d) CH3CHO + NH2OH CH3 – CH = N – OH

7 The correct order of reactivity towards electrophilic substitution is

(a) Benzoic acid > chlorobenzene > benzene > phenol
(b) Benzoic acid > phenol > benzene > chloro benzene
(c) Phenol > benzene > chlorobenzene > benzoic acid
(d) Phenol > chlorobenzene > Benzene > benzoic acid

8 For the following reactions :

–
(a) CH3CH2Cl + I W (b) (CH3)3C– Br + KCN(alc) X
(c) (CH3)2CH – Br + KOH(A) Y (d) (CH3)2CH– Br + KOH(alc) Z
Match the following :
W X Y Z
(a) CH3CH2CH2I (CH3)3CCN (CH3)2CHOH (CH3)2CHOH
(b) CH3CH2CH2I CH2= CH3 (CH3)2CHOH CH3 – CH=CH2

(c) CH3– CH=CH2 (CH3)3C – CN (CH3)2CHOH CH3–CH = CH2

(d) CH3CH2CH2I (CH3)3C – CN CH3 –CH=CH2 (CH3)2CHOH

9 Which of the following will hydrolyse most readily?

(a) (b) (c) (d)

10 The reactivity towards the addtion of HCl to:

(i) (ii) (iii)

(a) i > ii > iii (b) i > iii > ii (c) ii > i > iii
(d) ii > iii > i (e) iii > i > ii

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Key Concepts - 16

1 Increasing rate of reaction in a base catalyzed hydrolysis reaction:

(i) (ii) (iii) (iv)

(a) iii < ii < i < iv (b) ii < i < iv < iii (c) iv < i < ii < iii
(d) iv < iii < ii < i (e) i < iii < iv < ii

2 Increasing rate of reaction with an electrophile:

(i) (ii) (iii) (iv)

(a) iii > ii < i < iv (b) ii < i < iv < iii (c) ii < i < iii < iv
(d) iv < iii < ii < i (e) i < iii < iv < ii

3 Which reaction is kinetically (lowest G*)?

(a) HBr (b) HBr

(c) HBr (d) HBr

4 Which of the compounds below would react most rapidly with iodide ion in the SN2
reaction illustrated below?
acetone
R–Cl + I R–I + Cl

(a) CH 2CHCl2 (b) CH3 Cl

(c) (CH3)2CHCH2Cl (d)

5 Which of the reactions is a nucleophilic aromatic substitution?

(a) Reaction of 1-fluoro-3, 4-dinitrobenzene with ammonia.
(b) Nitrosation of N-methylaniline with sodium nitrite and HCl
(c) Reaction of benzoic acid with Br2 in the presence of FeBr3
(d) Reaction of benzyl ethyl ether with HBr (heat)
(e) Reaction of benzaldehyde with H2NOH

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6 Which one of the compound undergoes nucleophilic aromatic substitution at the
fastest rate?

(a) (b) (c)

(d) (e)

7 The following reaction is –

(a) SE2 (b) SN1 (c) SN2 (d) SN0

8 Which of the following reaction is dehydrohalogenation reaction

(a) C2H5Cl + a KOH CH2 = CH2 (b)

(c) CH3COOH + CH3OH CH3COCH3 (d) both (a) and (b)

9 Given reaction, C2H5Br + NaOH C2H5OH + NaBr is called:

(a) electrophilic substitution (b) nucleophilic substitution
(c) both (d) none

10 Which of the following is an example of elimination reaction?

(a) chlorination of CH4 (b) dehydration of alcohols
(c) nitration of benzene (d) hydroxylation of ethene

Key Concepts - 17
Br2
1 The reaction C6H6 C6H5Br + HBr is an example of:
FeBr3
(a) electrophilic addtion (b) electrophilic substitution
(c) nucleophilic substitution (d) free radical substitution
2 Which of the following undergo SN1 reaction?

(a) (b) (c) CH2=CH–Cl (d)

3 Which of the following is elimination reaction?

Alc.KOH
(a) CH2CH=CH.CH3

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(b) CH3CH2Cl + a KOH CH3CH2OH

(c)

(d) CH3– –CH2Br+Alc. KOH

CH3–C CH

4 Which of the following nucleophiles will show minimum reactivity towards S N2 reaction?

(a) Me3 (b) Me (c) (d) Me2CH

5 Which of the following is addition reaction?

(a) Br2 / CCl4 (b) Aq.KOH

Conc.H 2SO 4
(c) (d) HCN

6 The reaction
H 3PO 4
CH2=CH2+ H2O CH3CH2OH is known as:
300 50 º C
(a) a hydration reaction (b) addition reaction (c) substitution reactin
(d) oxoprocess

7 The correct order of reactivity towards electrophilic substitution is

(a) Benzoic acid > chlorobenzene > benzene > phenol
(b) Benzoic acid > phenol > benzene > chloro benzene
(c) Phenol > benzene > chlorobenzene > benzoic acid
(d) Phenol > chlorobenzene > Benzene > benzoic acid

8 Which one of the following will most readily be dehydrated in acidic conditon?

(a) (b) (c) (d)

9 Different hydrogen in C C =C –C 2–C 2–C (C 3)2 are representd by alphabets.

Arrange them in decreasing order of reactivity towards radical substitution.
(a) c > a > e > d > f > b (b) f > b > a > c > d > e
(c) b > c > a > f > d > e (d) a > b > c > d > e > f

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Key Concepts - 18
1 Which of the following statement is incorrect ?
(a) stability of singlet carbene is less than triplet carbene
(b) stability of singlet dichloro carbene is more than triplet dichloro carbene
(c) stability of singlet dichloro carbene is less than singlet diflouro carbene
(d) stability of singlet carbene is more than singlet dichloro carbene .

2 The order of activity of the various o - and p - directors is

(a) –O– > – OH > – OCOCH3 > –COCH3 (b) –OH > –O– > –OCOCH3 > –COCH3
(c) –OH > –O– > –COCH3 > –OCOCH3 (d) –O– > –COCH3 > –OCOCH3 > –OH

3 Aromatic compounds undergo.

(a) Nucleophilic substitution reaction (b) Electrophilic addition
(c) Electrophilic substitution (d) None of these

4 Among the following the correct decreasing order of reactivity towards nucleophilic
substitution follows:

(I) (II) (III) (IV) (V) (VI)

(a) VI > IV > V > III > II > I (b) V > VI > IV > II > III > I
(c) V > IV > VI > III > I > II (d) VI > V > IV > III > II > I

5 Which one of the following is a free-radical substitution reaction ?

Bolling
(a) + Cl 2

Anh.AlCl3
(b) + CH 3Cl

(c) + AgNO 2

(d) CH 3CHO HCN CH 3CH (OH )CN

6 Which of the following is the correct order of dehydrobromination of

(I) CH2–Br,, (II) (III) (IV)

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(a) I > II > III > IV (b) III > IV > II > I
(c) II > I > III > IV (d) II > IV > III > I

7 The order of reactivity of the following alcohols towards HCl is

(I) (II) (III) (IV)

(a) I > II > III > IV (b) I > III > II > IV (c) IV > III > II > I (d) IV > III > I > II

8 Consider the following reaction

‘X’ + HBr

Indentify the structure of major product ‘X’:

(a) (b)

(c) (d)

OH
(a) 2CH3CHO CH 3CHOHCH2CH O
(b) (C 6 H 5 ) 2 CHBr Ag 2O / H 2O (C 6 H 5 ) 2 CHOH AgBr

hv
(c) CH 3 CH CH 2 CH 2 N 2 CH 3 – +N2

H 2SO 4
(d ) CH 2 C CH 2 CH 3 COCH 3

14. DIPOLE MOMENT

Definition : The degree of polarity of a bond due to difference in electronegativity between

two adjacent atoms in the molecule is called dipole moment.
Dipole moment is represented by .
m = q × d where
q = magnitude of separated charge
d = The internuclear distance between two atoms

Dipole moment is represented by arrow head pointing towards electronegative atom.

Dipole moment depends on shape of the molecule

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Dipole moment of symmetrical compound is always zero.

Example :

Dipole moment of unsymmetrical compound is always greater than zero

More is the electronegativity of central atom of the molecule, more is the dipole moment

electronegativity of central atom is increasing hence is also increasing

Dipole moment of cis isomers is more than that of trans isomer.

If group has linear moments, then the dipole moment of the trans isomer will be zero.
Example :

=0

0, = 2.38 D

Key Concepts - 19

1 For which of the following molecules 0.

I II III IV
(a) only I (b) I & II (c) only III (d) III & IV

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2 I. II.

Which of the following statements are true about I and II

(a) I has more dipolemement that II due to –I effect and +M effect
(b) II has more dipole moment than I due to –I effect
(c) Due to steric inhibition of resonance in II dipole moment is more
(d) In I st structure ! value is less than IInd, so dipole moment value is more.

3 Which of the following has highest dipole moment:

(a) H–F (b) (c) (d)

4 The increasing order of dipole moment of the following compounds is :

(a) II > I > III (b) III > I > II (c) I > II > III (d) I > III > II

5 Arrange the following molecules in order of increasing dipole moment

(a) i < ii < iii < iv (b) i < iv < ii < iii (c) i < iii < ii < iv (d) iv < ii < iii < i

6 Which of the following is a compound most likely to have a dipole moment?

(a) CS2 (b) SO3 (c) H2S (d) SnCl4.

7 Which one of the following compounds will have the highest dipolemoment .

(a) NO (b) (c) (d)

2

8 Which of the following have dipolemoment

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(a) (b) (c) (d)

9 Which of the following more soluble in water

O
C–H
(a) (b) (c) (d)

10 Dipole moment of p-nitro aniline is

(a) greater than nitro benzene (b) lesser than nitro benzene
(c) greater than aniline (d) lesser than aniline

11 Which one of the following molecules will not have a permanent dipole ?
(a) CCl4 (b) CH2Cl2 (c) C2H5Cl (d) CHCl3 (e) CH3OCH3
12 The decreasing order of dipole moment of ortho(o), meta(m), para(p) chlorotoluenes is:
(a) o > m > p (b) p > o > m (c) p > m > o (d) m > o > p

13 The set in which the isomeric chlorotoulences have dipole moments 1.3D, 1.9D and
1.78D respectively, are

(a) (b)

(c) (d)

14 Which has definately zero dipole moment :

(a) (b) (c) (d)

15 Dipole moment of which of the following is maximum?

(a) NH 3 (b) NF3 (c) H 2O (d) OF 2

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15. INTER MOLECULAR ATTRACTION FORCES

Definition : The hydrogen bond is an electrostatic force of attraction between covalently

bonded hydrogen atom of one molecule and an electronegative atom (F,O, N) of another
molecule.
Example :
In hydrogen flouride, hydrogen is attached to strongly electronegative atom flourine. Hydrogen
accquires the positive charge which will be attracted electrostatically by the negative charge
on flourine in another molecule of HF.

Condition for hydrogen bonding

(a) The molecule must contain a highly electronegative atom linked to hydrogen atom.
(b) The size of electronegative atom should be small. F, O and N atoms only form
effective hydrogen bonding.
Factors affecting strength of hydrogen bonding
(1) Greater electronegativity of atom attached to hydrogen, the stronger is the hydrogeen
bond

(strength of hydrogen bonding)

(2) More is the crowding, strength of hydrogn bond is less

>

Types of hydrogen bonding

(1) Intermolecular hydrogen bonding: The hydrogen bonding between two molecules of same
compound
Example :

(a) (b)

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(c) (d)

(2) Intramolecular hydrogen bonding : The hydrogen bonding between two atoms of same
molecule. This type of electrostatic force of attraction is only possible if the ring size formed
on attraction is 5 or 6.
Example :

(a) (b) (c)

(d) (e)

Physical properties
(a) Boiling point : The boiling point of a liquid is the temperature where its kinetic
energy is sufficient to overcome the intermolecular attractive forces.
Boiling point Molecular weight
Intermolecular forces of attraction
In case of isomeric compounds, the boiling point depends on the surface area of the
compoud. More is the surface area of the compound, more will be boiling point of isomeric
compounds.
Example :
CH3–CH2–CH2–CH2–CH3 B.pt. = 36.1ºC
B.pt. = 27.9ºC

B.pt. = 9.5ºC

Boiling point decreases due to intramolecular hydrogen bonding

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B. pt = 178ºC ; B.pt = 217ºC

(b) Solubilities :
Solubility polarity
Polarity = surface area of hydrophobic part
More is the surface area of hydrophillic part, more is the solubility
Example :

As the surface area of hydrophillic part increases, solubility increases.

(c) Melting point
M.P molecular weight
Intermolecular forces of attraction
compactness
More is compactnes, more energy is required to seperate the molecules hence
melting point is more.
Compactness of symmetrical compounds is more.
Trans isomer is more compact than cis
branched hydrocarbons are more compact than linear hydrocarbons.
Example :

CH3–CH2–CH2–CH3

Key Concepts - 20

1 The order of melting point of ortho, para, metanitrophenol is –

(a) o > m > p (b) p > m > o (c) m > p > o (d) p > o > m

2 Decreasing order of boiling points amongst the following follows the order :
I. butanol - 1, II. butanol-2 III. 2-methyl-2-propanol

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(a) I > II > III (b) II > I > III (c) III > I > II (d) III > II > I

3 Which of the following would you expect to be the most volatile?

(a) (b) (c) (d)

4 Decreasing order of boiling points of CH3CH 2CHO, CH3CH 2CH2OH, CH3OCH2CH3 and
CH3CH2CH3 is
(a) CH3CH2CH2OH, CH3CH2CHO, CH3OCH2CH3, CH3CH2CH3
(b) CH3CH2CH2OH, CH3OCH2CH3, CH3CH2CHO, CH3CH2CH3
(c) CH3CH2CHO, CH3CH2CH2OH, CH3OCH2CH3, CH3CH2CH3
(d) none of these
5 The compound with highest melting point :

(a) (b) (c) (d)

6 Lowest boiling point of the following :

(a) (b) (c) (d)

7 The compound having highest melting point is :

(a) n hexane (b) cyclo hexane (c) cyclo hexanol (d) cyclo
hexanone
8 Which of the following has highest melting point .

(a) CH OH (b) CH O C H (c) CH NH (d) (CH ) O

3 3 2 5 3 2 3 2
9 The highest boiling point is expected from :
(a) Isooctane (b) n–octane
(c) 2,2,3,3–tetramethyl butane (d) 2 – methyl octane
10 Decreasing order of boiling points of n-pentanol (A), n-pentane (B), 3-pentanol (C) and
2,2-dimethyl propanol (D) is :
(a) A, C, D, B (b) B, D, C, A (c) C, A , D, B (d) None

Key Concepts - 21

1 Match the isomer with the appropriate boiling point

CH3CH2CH2CH2CH2NH2 CH3CH2CH2CH2NHCH3 CH3CH2CH2N(CH3)2
(a) 64 91 104
(b) 64 104 91
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(c) 91 64 104
(d) 104 91 64

2 Match the boiling points with the following three isomers of C4H10O2.
CH3OCH 2CH 2OCH 3 CH3CH 2OCH2CH2OH HOCH2CH2CH2CH 2OH
(a) 85ºC 230ºC 135ºC
(b) 230ºC 85ºC 135ºC
(c) 85ºC 135ºC 230ºC
(d) 135ºC 230ºC 85ºC
3 The order of solubility of the following compounds in water .
(I) CH3–CH2–CH2–CH2–OH (II) CH 3 (CH 2)5 CH 2OH

(III) HO CH2 CH 2 OH (IV) CH3 OH

(a) I > II > III > IV (b) IV > III > II > I
(c) III > IV > I > II (d) III > IV > II > I
4 Which substance would be expected to exibit the greatest surface tension at 25°C.
(a) CH3 – O – CH3 (b) C2H5 – OH
(c) CH3 – CH – (OH) – CH3 (d) HO – CH2 – CH2 – OH
5 Two molecules given below are capable of intramolecular hydrogen bonding. Which is likely to
form more stable hydrogen bond ?

(a) I (b) II (c) Both I and II will form equally stable H-bond. (d) none of these
6 The pair of molecules forming strongest intermolecular hydrogen bonds are

(a) and (b) and CHCl3

(c) H2O and H2O2 (d) CH3–CH2–NH2 and CH3–NH–CH3

7 Which is incorrect statement

(a) Dioxane boiling point is more than

(b) Boiling point of is less than

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(c) boiling point less

(d) n-hexanol boiling point more than

8 Which is correct order of boiling

(a) NO > O 2 > N 2 (b) CO < N 2 (c) BrCl < Br2 (d) N2 > O 2
9 Which of the following has high solubility in water

(a) (b) (c) (d)

10 Which of the following is/are correct statement/s

(a) is less acidic than

(b) Solubility in water is more for CH3CH 2CH2CH2OH than for

(c) Strength of H-bonding is more in –O–H.... than in –O–H....

(d) Second ionization energy of Li is more than the third ionization energy of Be
11 Which of the following undergo steam distilation

(a) (b) (c) (d)

12 Which of the following has highest density:

(a) (b) (c) (d)

13 Which of the following has highest density

2
(a) (b) (c) (d)

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14 Which of the polymer has highest melting point
(a) nylon 4 (b) nylon 6 (c) nylon 7 (d) nylon 11
15 Which of the polymer melts
(a) cotton (b) silk (c) wool (d) polyester

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ANSWER KEY
Key Concepts - 1

1. c 2. d 3. b,c,d 4. b 5. c 6. d
7. abcd 8. b 9. c 10. b

Key Concepts - 2

1. a,b,d 2. a,d 3. d 4. cd 5. d 6. c
7. (a) –I (b) –I (c) –I (d) +I (e) –I (f) +I
(g) –I (h) +I (i) –I (j) –I (k) –I

8. (a)

(b) – NH2 < – N H 3 (c) O H2 > – N H3

(d) –SO2–OH > –COOH (e) –COOH > –COOR (f) O H2 > – F

9. (a) N (CH 3 ) 3 > - NO2 (b) - NO2 > - CN

(c) CH Cl < CH Cl 2 < – CCl (d) F < CF
2 2 3 3

(e) , , , ,

10. (a) > –CH2 – (b)–CH2–CH2–CH2–CH3< –CH2–

Key Concepts - 3

1. b,c 2. d 3. b,c 4. d 5. a 6. abd

7. a 8. a,b 9. c 10. c

Key Concepts - 4

1. (a) –M (b) – M, +M (c) – M, +M (d) –M (e) + M

(f) +M, –M (g) –M, +M (h) –M (i) +M (j) –M
(k) No mesomerism (l) –M (m) –M (n) –M
(o) +M (p) –M (q) +M (r) –M (s) –M
(t) –M (u) –M (v) +M
8. (a), (b), (c), (g), (i) (k), (n) 9. (b), (d), (e), (g), (j)

10. (a) (b)

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(c) (d) (e)

(f) (g) (h)

(i)

Key Concepts - 5

1. (a) I < II (b) I > II (c) I > II (d) I > II (e) I > II
(f) I < II (g) I < II (h) I < II (i) I > II (j) I < II
(k) I > II (l) I < II (m) I < II (n) I < II (o) I > II
(p) I < II (q) I > II (r) I > II (s) I > II (t) I < II
(u) I < II (v) I < II (w) I > II (x) I < II

Key Concepts - 6
1. c 2. c 3. a 4. a 5. d 6. c
7. b 8. d 9. d 10. c

Key Concepts - 7

1. a 2. b 3. d 4. a 5. d 6. d
7. d 8. c 9. c 10. d

Key Concepts - 8

1. b 2. d 3. b 4. a 5. a 6. d
7. d 8. a

Key Concepts - 9

1. a 2. c 3. b 4. c 5. d 6. b
7. d 8. a
Key Concepts - 10

1. I < II < III 2. III > II > I 3. I > II > III > IV
4. d 5. b 6. d

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Key Concepts - 11

1. (A) (B)
(acid) (Base)

(C) (D)

(E)

(F)

2. (a) (b) (c) (d)

(e) (f) (g)

(h) (i) (j)

(k) (l) (m) CH3– – – –O–CH2–CH3

(n) (o) (p)

(q) HOCH2–CH2– (r) (s)

(t) (u)

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3. (a) (b) (c)

(d) (e) (f)

(g) (h) (i)

(j) (k) (l)

H
N H
(m) (n) (o)
N

H
H
O O
(p) CH –C–CH –C–H (q) (r)

(s) (t) (u) (u)

Key Concepts - 12
1. a 2. d 3. d 4. d 5. b 6. c
7. d 8. c 9. d 10. d
Key Concepts - 13
1. c 2. d 3. c 4. b 5. a 6. b
7. c 8. d 9. c 10. c
Key Concepts - 14 (A)

1. e 2. c 3. b 4. b 5. c 6. b
7. a,d 8. d 9. c 10. a
Key Concepts - 14 (B)
1. a 2. b 3. d 4. c 5. b 6. c
7. c 8. bcd 9. a 10. d 11. b 12. c
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Key Concepts - 15

1. b 2. b 3. c 4. b 5. c 6. c
7. c 8. b 9. c 10. e
Key Concepts - 16

1. c 2. c 3. d 4. a 5. a 6. b
7. c 8. a 9. b 10. b
Key Concepts - 17

1. b 2. b 3. ad 4. a 5. ad
6. b 7. c 8. a 9. a
Key Concepts - 18

1. d 2. a 3. c 4. d 5. a
6. b 7. c 8. b 9. bd
Key Concepts - 19

1. d 2. c 3. b 4. a 5. a 6. c
7. c 8. ab 9. b 10. ac 11. a 12. c
13. d 14. d 15. c
Key Concepts - 20

1. b 2. a 3. b 4. a 5. a 6. c
7. c 8. c 9. d 10. a

Key Concepts - 21
1. d 2. c 3. c 4. d 5. a 6. a
7. a 8. a 9. d 10. a,c 11. c 12. a
13. b 14. a 15. d

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EXERCISE-1
SINGLE CHOICE CORRECT TYPE QUESTIONS

1. Select the strongest acid in each of the following sets :

(i) (a) (b) (c) (d)

(ii) (a) (b) (c) (d)

(iii) (a) (b) (c) (d)

2. Arrange the given phenols in their decreasing order of acidity:

(I) C6H5–OH (II) F OH

(III) Cl OH (IV) O2N OH

Select the correct answer from the given code:
(A) IV > III > I > II (B) IV > II > III > I
(C) IV > III > II > I (D) IV > I > III > II

3. Which one of the following is the most acidic?

(A) (B) (C) (D) CH2=CH–CH3

4. Which one of the following phenols will show highest acidity?

(A) (B) (C) (D)

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5. The correct pKa order of the follwoing acids is :

(A) I > II > III (B) III > II > I (C) III > I > II (D) I > III > II
6. Arrange pH of the given compounds in decreasing order:
(1) Phenol (2) Ethyl alcohol (3) Formic acid (4) Benzoic acid
(A) 1 > 2 > 3 > 4 (B) 2 > 1 > 4 > 3 (C)3 > 2 > 4 > 1 (D) 4 > 3 > 1 > 2
7. Arrange acidity of given compounds in decreasing order:
(I) CH3–NH–CH2–CH2–OH (II) CH3–NH–CH2–CH2–CH2–OH

(III) (CH 3 )3 N CH 2 CH 2 OH
(A) III > I > II (B) III > II > I (C) I > II > III (D) II > I > III

8. Select the strongest base in following compound :

(i) (a) (b) (c) (d)

(ii) (a) (b) (c) (d)

(iii) (a) (b) (c) (d)

(iv) (a) (b) (c) (d)

9. Basicity order in following compound is :

(A) b > d > a > c (B) a > b > d > c (C) a > b > c > d (D) a > c > b > d

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10. Consider the following bases:
(I) o-nitroaniline (II) m-nitroaniline (III) p-nitroaniline
The decreasing order of basicity is:
(A) II > III > I (B) II > I > III (C) I > II >III (D) I > III > II

11. Consider the basicity of the following aromatic amines:

(I) aniline (II) p-nitroaniline (III) p-methoxyaniline (IV) p-methylaniline

The correct order of decreasing basicity is:
(A) III > IV > I > II (B) III > IV > II > I (C) I > II > III > IV (D) IV > III > II > I

12. Which one of the following is least basic in character?

(A) (B) (C) (D)

13. Hydrolysis of one mole of peroxo disulphuric acid produces

(A) Two moles of H2SO4
(B) Two moles of peroxo monosulphuric acid
(C) One mole of sulphuric acid & one mole of peroxo mono sulphuric acid
(D) One mole of sulphuric acid , one mole of peroxo monosulphuric acid & one mole of
H2O2

14. Amongst the following the most basic compound is

(A) Benzyl amine (B) Aniline
(C) Acetanilide (D) p- nitro aniline

15. Amongst the trihalides of nitrogen, which one is least basic ?

(A) NF3 (B) NCl3
(C) NBr3 (D) Nl3

16. What is the decreasing order of strength of bases.

(A) CH3 CH2 NH2 H C C OH

(B) H C C CH
3
CH2 NH2 OH

(C) OH NH2 H C C CH3 CH2

(D) NH2 H C C OH CH3 CH2

17. H2O is capable to act as an acid with

(A) NH3 (B) H2SO4
(C) C6H6 (D) HCl

18. Which of the following is Lewis acid

(A) PCl3 (B) AlCl3
(C) NCl3 (D) AsCl3

19. The strongest bronsted base in the following anions is

(A) ClO- (B) ClO2-
(C) ClO3- (D) ClO4-

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20. With reference to protonic acid which of the following statement is correct ?
(A) PH3 is more basic than NH3
(B) PH3 is less basic than NH3
(C) PH3 is equally basic than NH3
(D) PH3 is amphoteric while NH3 is basic

21. If pKb for F- at 25oC is 10.83 the ionisation constant of HF in water at this temperature
(A) 1.74 x 10-5 (B) 3.52 x 10-3
(C) 6.75 x 10 -4
(D) 5.38 x 10-2

22. The conjugate acid of NH2- is

(A) NH3 (B) NH2OH
(C) NH4+ (D) N2H4

23. The conjugate acid of S2O8-2 is

(A) H2S2O8 (B) H2SO4
(C) HSO4 (D) HS2O-8

24. The conjugate acid of HPO 24 is

(A) H2PO 4 (B) PO 34

(C) H3PO 4 (D) H3PO 3

25. Which of the following are amphiprotic in nature ?

(A) OH- (B) H2PO-2
(C) HSO3 -
(D) HF
26. Among the following compounds, the strongest acid is
(A) HC CH (B) C6H6
(C) C2H6 (D) CH3OH

27. The following acids have been arranged in order of decreasing acid strength. Identify
the correct order.
ClOH (l) BrOH (II) lOH(III)

(A) l> ll > lll (B) ll > I > III

(C) III > II > I (D) I > III > II
28. The conjugate acid of HF is
(A) F- (B) HF-2
(C) H2F+ (D) none of these

29. Which of the following species is an acid and also a conjugate base of another acid
(A) HSO-4 (B) H2SO4
(C) OH- (D) H3O+
30. Which of the following is the strongest acid
(A) H3PO4 (B) H3PO3
(C) H3PO2 (D) All have same strength

31. In the equilibrium CH3COOH + HF CH3COOH+2 + F-

(A) F is the conjugate acid of CH3COOH
-

(B) F- is the conjugate base of HF

(C) CH3COOH is the conjugate acid of CH3COOH+2
(D) CH3COOH+2 is the conjugate base of CH3COOH

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32. The conjugage base of [Cr(H2O)5Cl] is 2+

(A) [Cr(H2O)5]3+ (B) [Cr(H2O)4Cl]2+

(C) [Cr(H2O)4(OH)Cl]3+ (D) [Cr(H2O)4(OH)Cl]+

33. Correct order of acidic strength is

(A) Cl2O7 >SO2 > P4O10 (B) CO2 >N2O5> SO3
(C) Na2O > MgO >Al2O3 (D) K2O > CaO > MgO

34. Pyrophosphoric acid is a

(A) monobasic acid (B) dibasic acid
(C) tribasic acid (D) tetrabasic acid

35. Which among the following is the strongest base

(A) aniline (B) N, N dimethyl amine
(C) para nitro aniline (D) meta nitro aniline

36. Which of the following staements is/are correct

(A) l- is a weaker base than F-
.. ..
(B) H O: is a stronger base HN
2 :
.. ..
(C) HONH2 is a weaker base than NH3
(D) F3C: is a stronger base than Cl3C:

37. Which of the following orders regarding acid strength is correct ?

(A) HCOOH < CH3COOH < PhCOOH
(B) HCOOH > PhCOOH > CH3COOH
(C) HCOOH > CH3COOH > PhCOOH
(D) CH3COOH >HCOOH > PhCOOH

38. Which of the following statements is/are correct ?

(A) Maleic acid is a stronger acid than fumaric acid but maleate monoanion is a
weaker acid than fumarate monoanion
(B) Maleic acid is a stronger acid than fumaric acid and also maleate monoanion is a
stronger acid than fumarate monoanion
(C) Maleic acid is a weaker acid than fumaric acid but maleate monoanion is a
stronger acid than fumarate monoanion
(D) Maleic acid is a weaker acid than fumaric acid and also maleate monoanion is a
weaker acid than fumarate monoanion

39. Out of the following orders regarding basicity , which one is correct
(A) CH3CH2NH2 < PhCONH2 < CH3CONH2
(B) CH3CH2NH2 > PhCONH2 > CH3CONH2
(C) CH3CH2NH2 > PhCONH2 < CH3CONH2
(D) CH3CH2NH2 < PhCONH2 < CH3CONH2

40. Arrange the following ions in increasing order of acidity .

[Na(H2 O )n ] ,[ Al(H2 O ) 6 ]3 [Mn(H2 O ) 6 ]2 ,[Ni(H2 O ) 6 ]2
(I) (II) (III) (IV)
(A) I < II < III < IV (B) I < III < IV < II
(C) I < III < II < IV (D) II < IV < III < II

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41. Which of the following represent the resonating structure of

(A) (B) (C) (D) All of these

42. Which of the following resonance structure is minor contributor to the resonance hybrid ?

(A) I (B) II (C) III (D) all contribute equally

43. Which of the following is releasing group when in resonance ?

(A) –NH– –CH3 (B) –Cl (C) (D)

44. Which of the following can show both +M and –M effect ?

(A) –NH2 (B) –CH=CH 2 (C) –F (D)

45. Least contributing structure in nitroethene is

(A) (B) (C) (D)

46. Which of the following has longest C=C bond length ?

(A) (B)

(C) CH3CH2–CH=CH2 (D) all have equal C=C bond length

47. Which of the following is not resonating structure

(A) (B)

(C) CH2=CH–CH=CH 2 (D)

48. Arrange the following compounds in decreasing order of C–Cl bond length
(I) CH3–CH2–Cl (II) CH C–Cl (III) CH 2=CH–Cl
(A) I > II > III (B) III > II > I (C) I > III > II (D) II = I = III

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49. Which of the following is not a permissible resonating form

(A) (B) (C) (D)

50. Which of the following pairs represent resonating structure?

(A) (B) and

(C) and (D) both (B) and (C)

51. Which one of the following molecule has longest C=C bond length?
(A) CH2=C=CH 2 (B) CH 3–CH=CH2
(C) CH2=CH–CH2–CH=CH2 (D) CH2=CH–CH=CH2

52. W hich one of the following has all the effect nam ely inductive, mesomeric and
hyperconjugation?
(A) CH3–Cl (B) CH 2=CH–CH=CH 2

(C) (D) Ph– –CH3

53. Which will be least stable resonating structure ?

(A) 2 2 (B)

(C) (D)

54. Which of the following pairs is not a pair of resonating structures ?

(A) ,

(B) CH 3 – CH = CH – CH 3 , CH3 – CH 2 – CH = CH 2

(C) ,

(D) CH 3 – CH 2 – = N – CH3 , CH3 – CH 2 – C – CH 3

55. Which of the following statement is true about this molecule .

(A) C1 – C2 and C3 – C4 bonds are of same length

(B) C1 – C2 bond is shorter than C3 – C4 bond
(C) C1 – C2 bond is longer than C 3 – C 4 bond
(D) C1 – C2 and C 2 – C3 bonds are of same length

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56. Which will be least stable resonating structure ?

(A) (B) (C) (D)

57. (I) (II)

Ionisation of these compounds produces Br and

(A) same cation (B) different cation (C) same anion (D) different anion

58. Which of the following pairs of structures do not represent resonating structures?

(A)

(B)

(C) CH 2=C=O

(D)

59. Which of the following canonical form of O3 is not possible

(A) (B) (C) (D)

60. Which of the following is most unstable resonating structure of CH2= CH – CH = O.

CH2=CH–C O

(A) (B) (C) (D)

61. I. – CH=CH 2 II. – CH=CH–OCH 3 III. – CH=CH–NO2

Arrange these groups in decreasing order of their electron-donating power in resonance:
(A) II > III > I (B) III > II > I (C) II > I > III (D) III > I > II
O
||
62. I. – OH II. – O – C – CH 3 III. – NH 2
Arrange these groups in decreasing order of their electron-donating power in resonance :
(A) III > I > II (B) III > II > I (C) I > II > III (D) II > III > I

63. Resonance is not shown by :

(A) O3 (B) CO 2 (C) allene (D) vinyl chloride

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64. Heat of Hydrogenation of benzene and cyclohexene are –208 kJ/mol and –120 kJ/mol
respectively. The resonance energy of benzene is
(A) 102 kJ/mol (B) 32 kJ/mol (C) 152 kJ/mol (D) 88 kJ/
mol

65. The correct order of — — bond length is:

CH3– –Cl CH3– –OH CH3– –O– –CH3 CH3– –NH2 CH3– – ONa

I II III IV V

(A) IV > V > II > III > I (B) I < II < III < IV < V
(C) IV > II > V > III > I (D) V > IV > II > III > I

66. Highest heat of hydrogenation is observed with :

(A) 1, 3 – Penta diene (B) 1, 4 – Penta diene (C) 2, 3 – Penta diene (D) Cis – 2
– Pentene

67. Which one of the following has the smallest heat of hydrogenation per mole of double
bond.
(A) 1 – butene (B) trans–2–butene (C) cis–2–butene (D) 1–3–butadiene

68. Correct order of — — bond length is

I II III IV
(A) IV < I < II < III (B) IV < I < III < II (C) IV < II < I < III (D) IV < III < I < II
69. Weakest C H bond is found in :

(A) CH 3 CH2 CH3 (B)

(C) CH2 = CH CH3 (D) Ph CH2 Ph

70. Strongest C Cl bond is found in :

(A) CH2=CH CH2 Cl (B) CH 3 CH2 CH2 Cl (C) CH 2=CH Cl (D)

71. What is the correct order of stability of the following alkenes?

(1) CH2=CH 2 (2) CH 2=CHMe (3) Me2C=CHMe (4) Me2C=CMe2
(A) 1 > 2 > 3 > 4 (B) 3 > 4 > 2 > 1 (C) 2 > 4 > 1 > 3 (D) 4 > 3 > 2 > 1
72. Use the following data to answer the questions below:

H = –28.6 KCal mol–1

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H = –116.2 Kcal mol–1

Calculate the resonance energy of anthracene,

(A) 84 kcal/mol (B) 100 kcal/mol (C) 110 kcal/mol (D) 116 kcal/mol
73. Lone pair of pyridine is not delocalized with p-electrons because
(A) it is in p-orbital (B) it is in sp3-orbital
(C) it is in sp -orbital which is oriented at right angle to p-orbitals on carbon atoms.
2

(D) it is in sp-orbital which is orthogonal to p-orbitals on carbon atoms.

74. (I) (II) (III)

Stability order of these compounds is in the order as :

(A) I > II > III (B) I > III > II (C) III > I > II (D) II > I > III

75. The correct order of heat of hydrogenation is

(I) CH 2=CH–CH=CH 2 (II) (III) CH3–CH=CH–CH=CH 2

(A) I > II > III (B) II > I > III (C) II > III > I (D) III > II > I

76. The most stable carbocation amongst the following is :

(A) CH 3–CH2– C H 2 (B) CH 3– C H –CH2–CH3 (C) (CH 3)3 C (D) (CH 3)3C – C H 2

77. Which of the following intermediate have the complete octet around the carbon atom ?
(A) Carbanium ion (B) Carbonion ion (C) Free radical (D) Carbene

78. Most stable carbanion among the following is :

(A) (B) (C) (D)

79. Most stable carbocation is :

(A) CH 2 CH (B) (C) (D) CH3 – CH

CH
80. Correct order of stability of following carbanions is :

I II III
(A) I > II > III (B) III > II > I (C) I > III > II (D) III > I > II

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81. The stability of the given carbocations in decreasing order is :

I II III IV

(A) I > II > III > IV (B) IV > III > I > II (C) III > II > I > IV (D) II > III > IV > I

82. The most unstable carbocation is

(A) (B) (C) 2 (D)

83. Which of the following is more stable

(A) CH =CH (B) (C) (D)

84. The most stable contributor of the following canonicals are

(A) (B)

(C) (D)

85. The species having maximum electron deficiency is

(A) (B) (C) (D)

86. The decreasing order of stability of carbanions is :

(I) (II) (III) (IV)

(A) III > IV > I > II (B) III > IV > II > I (C) III > II > IV > II (D) IV > III > I > II

87. The most stable carbocation is

CH3
(A) CH –C–CH (B) (C) (D)

88. Ease of ionization to produce carbocation and will be maximum in which of the following
compounds :

(A) (B) (C) (D)

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89. Stability order of the following is in the order

(I) (II) (III) (IV)

(A) IV < II < III < I (B) IV < II < I < III (C) I < II < III < IV (D) IV < I < III < II

90. Which one is most stable free radical ?

(A) CH 2 CH (B) (C) (D) CH 2 CH C H 2

]91. Which one of the carbanions is most stable ?

(A) (B) (C) (D)

92. Which of the following three intermediates have nearly similar geometry?
(I) H2CH3 (II) : H 2CH3 (III) : H2COCH3 (IV) CH2=CH– H2
(A) I and III (B) II and IV (C) II , III and IV (D) I , III and IV

93. Least stable carbanion is:

(A) (CH3)3 C (B) NO 2– C H2 (C) (CN) 3 C (D) C 6H5– C H2

94. Which of the following will be least stable ?

(A) (B) (C) (D)

95. Which of the following carbocation is most stable ?

(A) (B) (C) (D)

96. Which allylic carbocation is the most stable carbocation ?

(A) CH3–CH=CH C H2 (B) CH3–CH=CH– C H–CH3

(C) CH3–CH= (D) All have same stability

(–)

97. (I) (II) (III)

Stability order of these anions is :

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(A) I > II > III (B) II > I > III (C) III > II > I (D) I > III > II

98. (I) (II) (III)

Stability order of these carbocation is:

(A) I > II > III (B) I > III > II (C) III > I > II (D) III > II > I

99. What is the increasing order of stability : OH– , NH 2– , H – C C – and CH3– CH2– .
(A) CH 3–CH2– < NH2– < H–C C – < OH –. (B) H–C C– < CH3– CH 2– < NH2– <OH –
(C) OH < H–C C < NH2 < CH 3–CH2
– – – –
(D) NH 2– < H–C C – < OH– < CH3–CH2–

100. Least stable carbanion is :

(A) C 6H5 C H2 (B) (CH3)3 C (C) C Cl3 (D) CH 3–
101. Which is most stable arenium carbocation?

(A) (B) (C) (D)

102. I II III

Stability order of these carbanions is :

(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III

103. I II III
Stability order of these carbanions is :
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > I > III

104. Which of the following C – H bond is weakest for homolytic fission?

(A) (B) (C) CH3–H (D)

105. The correct order of stability of following radicals is

(A) I > II > V > III > IV (B) IV > II > I > IV > III
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(C) IV > II > I > III > V (D) II > IV > I > V > III

(–)

106. (I) (II) (III)

Stability order of these carbanions is :

(A) III > II > I (C) I > II > III (C) II > III > I (D) II > I > III

107. The order of ease of removal of hydrogen

(A) H 1 > H4 > H3 > H2 (B) H 2 > H3 > H4 > H1

(C) H 3 > H 2 > H4 > H 1 (D) H 4 > H3 > H2 > H1

108. Which of the following is weakest acid?

(A) (B) (C) (D)

EXERCISE - 2
MULTIPLE CHOICE(S) CORRECT TYPE QUESTIONS

1. Hyperconjugation phenomenon is possible in

(A) CH3–CH=CH–CH=CH2 (B)

(C) (D)

2. Which of the following is true about resonance ?

(A) all resonating structure have same energy level.
(B) all resonating structure have same amount of net charge.
(C) all resonating structure have same number of unpaired electrons
(D) resonating structures have identical arrangement of atoms.

3. M effect takes part in

(A) unsaturated system containing conjugated double bond.
(B) Unsaturated system containing non conjugated double bond.
(C) A double bond in carbon chain adjacent to the lone pair
(D) Saturated system

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4. The group which exerts –I, –M & +M effect is/are
(A) –N=NH B) –SO2H (C) –NO 2 *(D) –N=CH 2

5. Which of the following groups when attached to benzene ring show – M effect

(A) (B) (C) –CH=CH 2 (D) –OCH3

6. Which of the following have delocalised electrons?

(A) (B) CH2=CH–O–CH=CH2

(C) (D) CH2–CH=CH–CH=CH2–

7. Which of the following order of resonance energy is/are correct?

(A) >

(B) >

(C) >

(D) CH 2=CH–NH–CH=CH2 > CH 2=CH–O–CH=CH 2

8. The correct order of stabilities are

(A) CH 3– –Cl > CH3– –F (B) >

(C) < (D) CO 3–2 > HCOO

9. Which of the following molecules exists as a resonance hybrid?

(A) Ph–CH=O (B) CH2=CH–NO (C) (D) 1,4-cyclohexadiene

10. Which of the following statements is true about the given compounds.
I. CH 2=CH–CH=CH–CH3 II. CH3–CH=C=CH–CH 3
(A) There is resonance in I but not in II (B) There is hyperconjugation in I but not in II.
(C) II has more canonical structure than I (D) Hyperconjugation takes place in both I and
II

11. Which of the following is not a resonating contributor for N 3H?

(A) (B) (C) (D)

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12. Pairs of structure which are resonance structures.

• •
(A) & CH 2= –H (B) CH 2=CH–CH=CH 2 & C H 2 –CH=CH– C H 2

NH 2 NH 2
| |
(C) CH2=CH–OH & CH3– C =O (D) CH3–CH2– C NH2 & CH 3–CH2 C
|
H
13. Which of the following pairs of structures does not represent resonance structure ?

(A) & (B) &

(C) & (D) &

14. In which of the following compounds nitrogen does not have sp3 hybridization

(A) (B) (C) (D)

15. Which of the following will have delocalisation

(A) (B) (C) (D)

16. Which of the following compound(s) is/are aromatic :

(A) (B) (C) (D)

17. Identify the group(s) which exert I , M & + M effects .

(A) NO2 (B) NH CO CH3 (C) N = O (D) CH = CH2

18. The group(s) that exert + M effects are :

(A) – O – – CH3 (B) – NH – – CH 3 (C) – N = O (D)

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19. Compare heat of combustion
I II

(A)

(B)

(C)

(D)

20. Which of the following carbocations can participate in delocalisation?

(A) (B) H CO (C) (D)

21. Which of the following carbocations are more stable than benzyl carbocation ?

(A) (B)

(C) (D)

22. Which of the following are the correct order of stability:

(A) < (B) <

(C) < (D) >

23. Planar cation is :

(A) N H 4 (B) C H 3 (C) CH3– C =O (D) (CH 3)3 C Sb F6( )

24. Which of the following statements is incorrect ?

(A) Allyl carbonium ion (CH 2=CH– ) is more stable than propyl carbonium ion.
(B) benzyl carbocation is more stable than t-butyl carbocation.
(C) vinyl carbocation is more stable than cyclohexyl carbocation.
(D) none of these

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25. Which of the following stability orders is correct?

(A) >

(B) >

(C) >

(D) >

26. Which of the following statements are true ?

(A) CH3O H2 is more stable than CH 3 H2,

(B) Me2 H is more stable than CH3CH2 H2,

(C) CH 2=CH– H2 is more stable than CH3CH2 H2.

(D) CH 2= is more stable than CH 3 H2.

27. In which of the following pairs of ions, the Ist ion is more stable:

(A) C6H5– and CH2=CH– (B) CH3– and CH2 =

I II I II

CH2
(C) and (D) and

I II I II

EXERCISE - 3
MATRIX MATCH
1. Match the following column
Column I (group) Column II (effect)

(A) (p) –M effect

(B) –CH2–CH3 (q) Hyperconjugation

CH3

(C) –C–CH (r) – I effect

CH3
(D) –C N (s) +I effect.
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2. Match the following column

Column I Column–II
(stability) (Effects which can explain
stability order)
(A) < (p) hyperconjugation

CH
(B) CH –C > (q) +M effect

CH
(C) > (r) –M effect

(D) CH –NO > (s) – I effect

3. Match the following column

Column I Column–II
(A) R–X + Y R–Y + X (p) Elimination
(B) RCH2CH2X RCH = CH2 + HX (q) Condensation
(C) CH3– CH3 CH3CH2CH2CH3 (r) Substitution

(D) RCH=O+ H2A RCH=A + H2O (s) Rearrangement

EXERCISE- 4
SUBJECTIVE TYPE QUESTIONS

1. Write correct order of acidic strength of following compounds:

(i) (a) H–F (b) H–Cl (c) H–Br (d) H–I

(ii) (a) CH4 (b) NH3 (c) H2O (d) H–F

(iii) (a) CH3–CH2–O–H (b) CH 3 CH O H (c)

|
CH 3

(iv) (a) F–CH2–CH2–O–H (b) NO2–CH2–CH2–O–H

(c) Br–CH2–CH2–O–H (d) NH3 CH2 CH2 O H

2. Write correct order of acidic strength of following compounds:

(i) (a) CH3COOH (b) CH3CH2OH (c) C6H5OH (d) C6H5SO3H

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(ii) (a) (b) (c)

COOH CH 2 COOH
(iii) (a) | (b) (c) |
COOH CH 2 COOH

3. Write correct order of acidic strength of following compounds:

O O Cl O
|| || | ||
(i) (a) Cl CH 2 C O H (b) Cl CH C O H (c) Cl C C O H
| |
Cl Cl

O O
|| ||
(ii) (a) CH 3 CH 2 CH C O H (b) CH 3 CH CH 2 C O H
| |
F F
O
||
(c) CH 2 CH 2 CH 2 C O H
|
F
O O
|| ||
(iii) (a) NO 2 CH 2 C O H (b) F CH C O H
2

O O
|| ||
(c) Ph CH 2 C O H (d) CH 3 CH 2 C O H
4. Write correct order of acidic strength of following compounds:

(i) (a) (b) (c)

(ii) (a) (b) (c)

(iii) (a) (b) (c) (d)

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5 Write correct order of acidic strength of following compounds:

(i) (a) (b) (c) (d)

O–H O
N
(ii) (a) (b) O (c) (d)

6 Write correct order of acidic strength of following compounds:

(i) (a) (b)

(ii) (a) (b)

(iii) (a) (b) (c)

(iv) (a) (b) (c)

7. Say which pka belong to which functional group in case of following amino acids :

(i) cysteine : 1.8, 8.3 & 10.8

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(ii) glutamic acid : : 2.19, 4.25, 9.67

8. Record the following sets of compounds according to increasing pKa ( = – log Ka)

(a) , , cyclohexane carboxylic acid.

(b) 1-butyne, 1-butene, butane

(c) Propanoic acid, 3-bromopropanoic acid, 2-nitropropanoic acid
(d) Phenol,o-nitrophenol, o-cresol
(e) Hexylamine, aniline, methylamine
9. Explain which is a stronger acid.
O O
|| ||
(a) CH3CH3 BrCH2NO2 (b) CH 3 C CH 3 & CH3 C CH 2CN
(c) CH3 – CHO CH3 – NO2
10. Explain which is a weaker acid.

(a) or (c) or

(b) or

11. Which of the following would you predict to be the stronger acid ?

(a) or

(b) CH3 – CH2 – CH2 – OH or CH3 – CH = CH – OH

(c) CH3 – CH = CH – CH2 – OH or CH3 – CH = CH – OH

12. Write increasing order of basic strength of following:

(i) (a) F (b) Cl (c) Br (d) I

(ii) (a) CH 3 (b) NH 2 (c) OH (d) F

(iii) (a) R–NH2 (b) Ph–NH2 (c) R C NH 2

||
O
(iv) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (Gas phase)

(v) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (in H2O)

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13. Write increasing order of basic strength of following:

(i) (a) (b) (c)

(ii) (a) (b) (c)

(iii) (a) (b) (c)

(iv) (a) (b) (c) (d)

14. Write increasing order of basic strength of following:

(i) (a) CH3–CH 2– N H 2 (b) CH3–CH= NH (c) CH3–C N

(ii) (a) CH 3 C NH 2 (b) CH3–CH2– NH 2 (c) CH 3 C N H 2 (d) N H 2 C N H 2

|| || ||
O NH NH

NH

(iii) (a) (b) (c)

(iv) (a) (b) (c)

(v) (a) (b)

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15. Write increasing order of basic strength of following:

(i) (a) (b) (c) (d)

(ii) (a) (b) (c)

(iii) (a) (b) (c)

(iv) (a) (b) (c)

NMe

(v) (a) (b) (c)

OMe

16. Arrange the following compound in decreasing order of their basicity.

(i) (a) H2C = CHNa (b) CH3CH2Na (c) CH3CH2ONa (d) HC CNa

(ii) (a) (b) (c) (d)

(iii) (a) HO¯ (b) NH3 (c) H2O

17. In each of the following pair of compounds, which is more basic in aqueous solution? Give an
explanation for your choice:

(a) CH3NH2 or CF3NH2 (b) CH3CONH2 or H2N NH2

(c) n-PrNH2 or CH3CN (d) C6H5N(CH3)2 or 2,6-dimethyl-N-N-dimethylaniline
(e) m-nitroaniline or p-nitroaniline

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18. From the following pair, select the stronger base:
(a) p-methoxy aniline or p-cyanoaniline
(b) pyridine or pyrrole
(c) CH3CN or CH3CH2NH2

19. Choose the member of each of the following pairs of compunds that is likely to be the weaker
base.
(a) H2O or H3O (b) H2S, HS–, S2– (c) Cl–, SH–
(d) F–, OH–, NH2–, CH 3 (e) HF, H2O, NH3 (f) OH–, SH–, SeH–

20. Explain which compound is the weaker base.

(a) or (b) CH2 = CH – CH = CH – CH2– or CH2 = CH – CH2–

O O O O
|| || | | ||
(c) O C C OH or HO C C OH (d) or

21. Rank the following amines in increasing basic nature.

(a)

(i) (ii) (iii) (iv)

(b)

(i) (ii) (iii) (iv)

22. Arrange the basic strength of the following compounds.

(a) OH – CH3COO – Cl–

(i) (ii) (iii)

(b) CH C– CH2 = CH– CH3CH2–

(i) (ii) (iii)

(c) CH2 = CHCH2NH2 CH3CH2CH2NH2 CH C – CH2NH2

(i) (ii) (iii)

23. Arrange the basic strength of the following compounds.

(a)

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(i) (ii) (iii)

(b)

(i) (ii) (iii)

NH NH NH
(c)
HC ON
(i) (ii) (iii)

24 Arrange the following compounds in order of increasing basicity.

(a) CH3NH2, CH3 NH 3 , CH3NH—
(b) CH3O—, CH3NH—, CH3 CH 2
(c) CH3CH = CH—, CH3CH2 CH 2 , CH3C C—

25 Rank the amines in each set in order of increasing basicity.

(a)

(b)

(c)

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ANSWER KEY
EXERCISE - 1

1. (i) b (ii) a (iii) b 2. C 3. B 4. C

5. B 6. B 7. A 8. (i) d (ii) b (iii) a (iv) a
9. B 10. A 11. A 12. A 13. C 14. A
15. A 16. A 17. A 18 B 19. A 20. B
21. C 22. A 23. D 24. A 25. A 26. A
27. A 28. C 29. A 30. C 31. B 32. D
33. A 34. D 35. B 36. A, C, D 37. B
38. A 39. A 40. B 41. D 42. B 43. A
44. B 45. C 46. A 47. B 48. C 49. C
50. D 51. B 52. D 53. A 54. B 55. B
56. C 57. A 58. A 59. C 60. A 61. C
62. A 63. C 64. C 65. D 66. D 67. C
68. A 69. D 70. C 71. D 72. A 73. C
74. B 75. A 76. C 77. B 78. D 79. C
80. B 81. C 82. C 83. B 84. B 85. D
86. A 87. B 88. B 89. A 90. B 91. B
92. C 93. A 94. B 95. A 96. C 97. A
98. A 99. A 100. B 101. C 102. C 103. A
104. D 105. C 106. A 107. B 108. B

EXERCISE - 2
1. ACD 2. BCD 3. BC 4. ABD 5. BC 6. ABD
7. ABCD 8. BC 9. AB 10 . AD 11 . BC 12 . AD
13 . AB 14 . ABC 15 . BCD 16 . BCD 17 . CD 18 . ABCD
19 . (a) I < II (b) I > II (c) I > II (d) I > II
20 . BD 21 . ACD 22 . BCD 23 . BCD 24 . BC 25 . BCD
26 . ABC 27 . AC

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EXERCISE - 3

1. a – r, b – q s, c – s , d – pr 2. A - r, B - p, C - q, D - rs.
3. A-r, B-p, C-s, D-q

EXERCISE - 4
1 (i) d>c>b>a (ii) d>c>b>a (iii) a > b > c (iv) d>b>a>c
2 (i) d > a > c> b (ii) c > b > a (iii) a > b > c
3 (i) c > b > a (ii) a > b > c (iii) a > b > c > d
4 (i) a > b > c (ii) a > b > c (iii) d > b > c > a
5 (i) c > a > b > d (ii) d > c > a > b
6 (i) b > a (ii) b > a (iii) c > b > a (iv) c > a > b

7. (i) cysteine : (ii) glutamic acid :

8. (a) 3<2<1; (b) 1<2<3; (c) 3<2<1; (d) 2<1<3; (e) 2<3<1
9. (a) 2; (b) 2; (c) 2 10. (a) 2; (b) 2; (c) 2 11. (a) 2; (b) 2; (c) 2
12. (i) a > b > c > d (ii) a > b> c> d (iii) a > b> c (iv) a < b< c< d

(v) c > b> d> a

13. (i) a < b < c (ii) c > a > b (iii) b > c> a (iv) c > d> b > a
14. (i) a > b > c (ii) d > c > b > a (iii) b > c > a (iv) c > b > a
(v) b > a
15. (i) d > c > b > a (ii) c > b > a (iii) b > a > c (iv) a > b > c
(v) c > a > b
16. (i) b > a > d > c (ii) b > a > c > d (iii) a > b > c
17. (a) i, (b) ii, (c) i, (d) ii, (e) i 18. (a) i, (b) i, (c) ii
19. (a) 2; (b) 1; (c) 1; (d) 1; (e) 1; (f) 3 20. (a) 2; (b) 1; (c) 2; (d) 2
21. (a) 3<2<1<4; (b) 1<2<3<4 22. (a) 1>2>3; (b) 1<2<3; (c) 3<1<2;
23. (a) 2<1<3; (b) 1<2<3; (c) 2 > 1 > 3 24. (a) 2<1<3; (b) 1<2<3; (c) 3<1<2
25. (a) 2 > 1> 3, (b) 1 > 2> 3, (c) 1 > 3 > 2,

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 CH-13 ISOMERISM

CHAPTER-13
ISOMERISM
Different organic compounds with the same molecular formula but different physical and chemical
properties are called isomers and the general phenomenon is known as isomerism. It is classified
as follows.
ISOMERISM

Stereoisomerism
Structural
(constitutional)
Isomerism

Chain Position Functional Metamerism Ring Chain Tautomerism

Confirmational Configurational

Optical Geometrical
Structural Isomerism
Compounds which possess the same molecular formula but differ in bonding arrangement of
atoms (or) groups within the molecule i.e. differ in connectivity of atoms.

(i) Chain or Nuclear Isomerism: In this type the isomers differ in the variation of the carbon chain
(or) skeleton of the molecule. The same molecular formula may represent a straight chain of
carbons as well as a branched chain. The molecular formula C 4H10 stands for two isomers
namely n-butane and isobutane.
H3C CH3
CH
CH 3CH 2 CH 2CH 3  and 
n  Bu tan e
CH3
isobutane (2 methyl propane)

C5H12 stands for three chain isomers

(i) CH 3CH 2 CH 2 CH 3CH 3 
(n-pentane)

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 CH-13 ISOMERISM
CH3

CH CH3

(ii) H3C CH2
isopentane

CH3
(iii) H3C C CH3 
CH3
neopentane (2,2-dimethyl propane)

Cyclohexane and methyl cyclopentane are nuclear isomerism

CH3
CH2
H2C CH2 CH
H2C CH2
( nuclear )
H2C CH2 H2C CH2
CH2

C 4H 10 O
CH3

OH
H3C OH and H3C
butan-1-ol 2-methylpropan-1-ol

Illustration 1 :
Give the possible chain isomers for propyl benzene.
Solution :
H3 C CH3
CH 2CH 2CH 3

propylbenzene isopropylbenzene

Illustration 2 :
Give the possible chain isomers for C5H13N
Solution :
NH2
H3 C CH3

H3 C NH2 H3 C

CH3 NH2
CH3

(ii) Position Isomerism : In this, the isomers differ in the attachment of the functional group (or)
substituents to the carbon chain. This is illustrated by the following examples.

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 CH-13 ISOMERISM

(a) CH3CH 2 CH  CH 2  and CH 3  CH  CH  CH 3 

but-1-ene but-2-ene
Cl
Cl and H3C
(b) H3C
1-chloropropane CH3
2-chloropropane
CH3

(c) H3C CH3 and H3C CH3

3-methylpentane
CH3
2-methylpentane

Illustration 3 :
Give the possible positional isomerism for di chlorobenzene.
Solution :

Cl Cl Cl
Cl

Cl
1,2-dichlorobenzene 1,3-dichlorobenzene
Cl
1,4-dichlorobenzene

Note : In the aromatic series, the disubstitution products of benzene also exhibit isomerism due
to different relative positions occupied by the two substituents on the benzene ring.

(iii) Functional Isomerism : If the molecules have the same molecular formula but differ in the
type of the functional group , then it is known as functional group isomerism. A few examples of
functional isomers are:
(a) Molecular p-alcohol s-alcohol t-alcohol Ethers
formula
H3C H3C O

C2 H6 O OH1 –– –– CH3
ethanol dimethyl ether

H3C
H3 C O
OH OH
C3 H8 O H3C –– CH3
H3C

CH3
OH
H3C CH3
C4H10O H3C OH CH3
H3C
OH

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 CH-13 ISOMERISM
CH3 H3C O
O CH3
OH H3 C CH3
H3C H3C

(b) Monocarboxylic acids and esters are functional isomers

H3C O

OH and H3C

O O
propanoic acid
H3C
methyl acetate
(c) Aldehydes, ketones, unsaturated alcohols and alkene oxides are functional isomers.

H3C H2C O
(i) C 2H4 O OH
O Ethylene oxide
Ethanal Vinyl alcohol
O
H3C H2C
H3C OH
(ii) C 3H6 O
O CH3 Allyl alcohol
Propanal Propanone

(iii) Cyanides are isomeric with isocyanides

RCN (Alkyl cyanide) RNC (alkyl isocyanide)
(iv) Nitroalkanes are isomeric with alkyl nitrites
O
R O
R N
N O
O
Nitroalkane Alkyl Nitrite
(v) Aromatic alcohols may be isomeric with phenols
OH
CH3

OH

phenylmethanol o-cresol

(vi) Sometimes a double bond containing compound may be isomeric with a triple
bond containing compound. This is also called as functional isomerism. Thus
butyne is isomeric with butadiene (Molecular formula C4H6)
H3C H2C

CH CH2
but-1-yne buta-1,3-diene

(vii) Primary, secondary and tertiary amines of some molecular formula are also the
functional isomers.

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 CH-13 ISOMERISM
CH3
H 3C H 3C NH
H 3C N
NH2 C 2 H5
CH3
propan-1-amine N,N,N-trimethylamine
N-ethyl-N-methylamine

Illustration 4 :
Give the functional isomer for acetic acid
Solution :
O O

H3C H

OH O CH3
acetic acid methyl formate

Monocarboxylic acids and Ester’s are functional isomers.

Illustration 5 :
Give the functional isomer for acetaldoxime.
Solution : O
H3 C
H3 C
N OH
NH2
(1E)-acetaldehyde oxime
acetamide

Oximes and amides are functional isomers.

Illustration 6 :
Give the functional isomer for ethyl thioalcohol.
Solution :

H3 C H 3C S

S H CH3
ethanethiol (methylthio)methane

Thioalcohols and thio ethers are functional isomers.

(iv) Metamerism : It arises when different alkyl radicals are joined with the same divalent functional
group present in the molecule, e.g. ethers, thioethers, secondary amines, ketones, esters etc.

H3 C O
O CH3
(a) H3C O CH3 H3 C CH3
diethyl ether H3 C
1-methoxypropane
2-methoxypropane

H 3C S
S
CH3
(b) H3 C S CH3 H3 C CH3
1-(methylthio)propane H 3C
(ethylthio)ethane
2-(methylthio)propane

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 CH-13 ISOMERISM
Illustration 7 :
Give the metamer for ethyl propionate.
Solution :
O

O CH3 CH3
H3C H3C O
propyl acetate
O
ethyl propionate
(v) Ring Chain Isomerism : This type of isomerism is due to difference in way of linking of carbon
atoms and the isomers may have either open chain (or) closed chain structure e.g. alkenes and
cycloalkanes.
(a) C 3H 6

H3C
CH2
cyclopropane
prop-1-ene

(b) C 4H 8

CH2
H3 C H3 C
H3 C CH3
CH2 CH3
CH3 cyclobutane methylcyclopropane
but-1-ene but-2-ene
2-methylprop-1-ene

(c) C 6H 12

H3C CH3
CH2
hex-1-ene
cyclohexane methylcyclopentane
Note: Ring chain isomers are always functional isomers.

TAUTOMERISM
It is a special type of functional isomerism in which the isomers are readily interchangeable and
maintain a dynamic equilibrium with each other. Hence, the name dynamic isomerism. Both the
isomers represent one and a single substance. Reversibility of change is due to mobility of a
group or atom which can move from one position to another in the molecule, often with
rearrangement of a double bond. These two forms are called tautomers or tautomerides of
each other.

Various terms used for tautomerims

(a) Desmotropism [ desmos = bond ; tropos = turn , (From Greek) ]
(b) Pseudomerism (c) Kryptomerism
(d) Metamerism (e) Allelotropism

Structural requirement for tautomerism

(i) Compound should have electronegative atom bonded with multiple bond (i.e. N and O).
(ii) Compound should have atleast one acidic hydrogen present on -carbon of the molecule.
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 CH-13 ISOMERISM

It the compound favour these two conditions it will show tautomerism. For example.
O O
 Electronegative atom  Electronegative atom
H3 C H3 C

H CH3

 Electronegative atom
H3 C N Electronegative atom

N O H 3C
CH3
O

These compounds fulfill both the conditions, hence these will show tautomerism.
CH3 O C6H5 O C6H5

H3 C H3 C N H5C6

 CH3 H  C 6 H5 O  CH3 N

In these compounds electronegative atom is bonded with multiple bond but compound has no
hydrogen on -carbon hence these compounds will not show tautomerism.
If compound has active methylene group (or) active methyne group then -carbon for tautomerism
is always carbon of active methylene (or) methyne group. For example
O

H3 C O
 O CH 2 O  CN
CH 2 HC

NC CH 2
H 5C 2 OOC CH3 CH3 H3 C CH3
CN
active methylene group active methylene group active methylene group

These compounds will also show tautomerism because these compounds fulfill both structural
requirements.
Cause of tautomerism : Migration of acidic hydrogen from -carbon to electronegative atom
which is bonded with multiple bond is the cause of tautomerism and this phenomenon is known
as tautomerism.
OH
CH3 H2 C
H
CH3
O
(I) (II)
(i) Both (I) and (II) are isomers known as tautomers.
(ii) Tautomers always be in equilibrium state.
(iii) Number of sigma, pi and lone pair of electrons in both tautomers are always same.
(iv) Tautomerism is a chemical phenomenon which takes place only in liquid state.
(v) Tautomersim is catalysed by acid as well as base.
(vi) Tautomers are always reversible functional groups, functional isomers.

Difference between tautomerism and resonance

• Tautomers of a compound actually exist and can be separated. On the other hand, resonating
structures are imaginary and question of separation of such structure even does not arise.
• Tautomers are different in the position of at least one atom relative to other atoms in the molecule.

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 CH-13 ISOMERISM

Chief difference is the position of electrons and -electrons or unshared e¯ not the
atom.
• Position of ions in tautomers differ in bond length, i.e., migratory part has different bond lenghts
in two cases of its attachment in appreciable difference. In resonating structure, difference is not
more than 0.3Å, i.e., two extreme case in benzene are 1.54Å and 1.33Å.
• Tautomers are in dynamic equilibrium interconvertible and no such equilibrium in
resonance.
• Tautomerism has no contribution on stabilization of a molecule resonance has its effect on
stabilization.
• Tautomerism may occur in planar or non-planar while resonance only in plannar.

Tautomerism is of several types the two important types are dyad and triad systems :
(a) Dyad System: It involves the oscillation of H atom between two polyvalent atoms, e.g.., hydrogen
cyanide (I) and hydrogen isocyanide (II).
H C N H N C
(I) (II)

In the above example the H atom vibrates between carbon and nitrogen atoms. The alkyl derivatives
of (I) are called cyanides while those of (II) isocyanides.

(b) Triad System: In it one H atom oscillates between three polyvalent atoms.
(i) Keto-enol tautomerim : In this case the polyvalent atoms are one oxygen and two
carbon atoms, e.g. aceto acetic ester, acetyl acetone, benzoyl acetone, acetaldehyde,
acetone, phenol etc.
The form containing keto (oxo) group is called keto while that having alkene and –ol
functions is called an enol form.
H
H3 C O
O O
C 2 H5
C 2 H5
OH O
CH3 O
keto form enol form

H3 C CH3 H3 C CH3

O O OH O
keto form enol form

H 5C 6 CH3 H5C6 CH3

O O OH O
keto form enol form

The conversion of a keto form into enol form is known as enolization. It is catalysed by the
presence of acid (or) alkali. This dynamic isomerism is shown only by those aldehydes, ketones
or esters which have at least one labile -hydrogen atom. For example, benzaldehyde and
benzophenone do not have labile -hydrogen, hence these do not show tautomerism.

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 CH-13 ISOMERISM
O O

H 5C 6 H5C6 (absence of  -H atom)

H C 6H 5

On other hand, acetophenone contains -H atoms, hence exhibits tautomerism.

O OH

H 5C 6 H 5C 6

CH3 CH2
Keto form Enol form

Enolization is in the following order:

CH3COCH3  CH3COCH2COOC2H5  C6H5COCH2COOC2H5
 CH3COCH2CHO  CH3COCH2COCH3
In compounds whose molecules have two carbonyl groups separated by one – CH 2 – group
(called -dicarbonyl compounds), the amount of enol present at equilibrium is far higher e.g.
OH O
O O

H 3C CH3
H3 C CH3
(76%)
(24%)
The greater stability of the enol form of -dicarbonyl compounds can be attributed to stability
gained through resonance stabilization of the conjugated double bonds and (in a cyclic form)
through hydrogen bonding.
H H
O O O O

H3 C CH3 H3 C CH3

H H
Percentage of enolic contents of some common compounds in decreasing order is given below:
O O O O O

H5C 6 CH3 H3C CH3

O O
O O
O O

H3C CH3 H3C

H3C
H3C O

C 2H5
Percentage Composition of Tautomeric Mixture : Percentage of enol contents of some
compounds is given below in the table.

Enol content of some compounds

Compound Enol Compound Enol Percentage

Percentage
O O O

H 3C
0.00025 H3C CH3 80.4
CH3

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 CH-13 ISOMERISM
O
O O
CH3
H3C 0.0056 89.0
H 5C 6 CH3
O

O O O

H3C O 4.8 99.99

CH3

The conversion of a keto form into an enol form is known as enolisation and the enolisation of a
compound has been found to depend upon various factors such as structural factor, temperature
and nature of solvent. However, the most important is the structural factor (resonance and hydrogen
bonding).

(a) Ketonic form predominates in simple monocarbonyl compounds like acetaldehyde, acetone and
cyclohexanone. This is due to the greater bond strength of C = O {>C = O, 365 kJ/mole) present
in keto form than the carbon-carbon double bond (C = C, 250 kJ/mole) present in enolic form.

(b) Enolic form predominates in -di ketones due to intramolecular hydrogen bonding and resonance.
Intramolecular hydrogen bonding stabilizes enol form by 7 kcal/mole and resonance stabilizes
enol form by 15 kcal/mole. Thus enol form is more stable than keto form by 22 kcal/mole in 1,3-
diketones.
O O
H H
O O O O
H3 C CH3
H3 C CH3 H3 C CH3

H H H H
O O O O O O O O

H3 C CH3 H3 C CH3 H 3C CH3 H3 C CH3

(ii) Triad System containing Nitrogen

(a) Nitrous acid exists in two tautomeric forms:
O
H O
H N
N O
O
Nitrite form
Nitro form
The alkyl derivatives of nitro form and nitrite form are called as nitro alkanes and alkyl
nitrites, respectively.

(b) Primary and secondary nitroalkanes have liable -H atom, hence exhibit nitro-aci nitro
type of tautomerism.

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 CH-13 ISOMERISM

H3C
 H3C

N O N OH

O O
Nitro form (I) Aci form (II)
(c) Nitroso-oximino System: In this system one tautomer exits as nitroso while the other
tautomer exists as an isonitroso (oxime) form.

OH
O
H3C N
H3C N
Nitroso form Isonitroso form

(d) Imine-Enamine System

H 3C H 3C
NH NH2
Im in e E n am in e

(e) Diazo-amino: Triazen system or Mesohydric tautomerism:

3 2 1
– N = N – NH NH – N = N

diazoamino Diazoamino

(f) Diazo-nitrosamine system :

3 2 1
Ar – N = N – OH Ar – NH – N = O
Diazo Nitrosoamine

(g) Three carbon system:

– CH – C = C C=C–C–H

3 2 1
[CH3CH = CHCH2Br CH3CH – CH = CH2

Br
CH3CH = CH – CH2 CH3 – CH – CH = CH2]

Mechanism of tautomerism : Acid catalysed tautomerism is a two step process.

(i) Proton transfer from the acid catalyst, H—A, to the carbonyl oxygen forms the conjugate acid of
the aldehyde (or) ketone.
O O H

H3C C CH3  H—A

fast
H3C C CH3  :A
(conjugate acid of ketone)
(ii) Proton transfer from the  -carbon to the base, A gives the enol and generates a new molecule


of the acid catalyst, H—A.

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 CH-13 ISOMERISM

O H OH

H3C C CH2 H
slow
H3C C CH2  H—A
Enol form
with unsymmetrical ketones, enolization may occur in either of two directions.

OH O OH
 
H2C C CH2 CH3 H3C C CH2 CH3 H3 C C CH2 CH3
but-1-en-2-ol 2-Butanone but-2-en-2-ol

the ketone is by far the most abundant species present at equilibrium. Both enols are also present,
but in very small concentrations. The enol with the more highly substituted double bond is themore
stable of the two enols and is present in higher concentration than the other.

* Percent enol content  conjugation

/ Temperature
/ Hydrogen bonding
/ Base strength

Key Concepts - 1

1 The total number of possible isomer’s for acetone is:

(a) 2 (b) 7 (c) 5 (d) Can’t say

2 CH2=CH–CH2–CH3 and CH3–C=CH2 are:

CH3
(a) chain isomers (b) Position isomers (c) functional isomers (d) Metamers

3 CH3–CH2–OCH2–CH2–CH3 and CH3–OCH2–CH2–CH2–CH3

(a) chain isomers (b) position isomers (c) functional isomers (d) metamer’s

4 Neopentane and isopentane are which of the following types of isomer

(a) chain (b) position (c) functional (d) metamer

5 o-cresol, p-cresol & m-cresol are–

(a) chain isomers (b) position isomers (c) functional isomers (d) None of tehse

6 Which of the following is an isomer of acetaldehyde:

(a) vinyl alcohol (b) vinyl methyl ether (c) Epoxy ethane (d) (a) and (c) both

7 1,3-butadiene and 2-butyne are:

(a) Chain isomer (b) Position isomer (c) Functional isomer (d) None of these

8 The compound CH3–CH2–COOH and CH3–CH2–CHO are:

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 CH-13 ISOMERISM
(a) chain isomers (b) position isomers
(c) functional isomers (d) None

9 Esters are functional isomers of

(a) Hydroxy aldehyde (b) Ketone (c) diketone (d) diol

10 Which of the following are isomers

(a) Ethanol and ethoxy ethane (b) Methanol and methoxy methane
(c) Propanoic acid and ethyl acetate (d) propionaldehyde and acetone

11 Number of isomeric forms of C7H9N having benzene ring will be:

(a) 7 (b) 6 (c) 5 (d) 4

12 How many isomers of C5H11OH will be primary alcohol

(a) 2 (b) 3 (c) 4 (d) 5

13 Which is not found in alkenes:

(a) chain isomerism (b) Structural isomerism
(c) Metamerism (d) Position isomerism

14 and show isomerism

(A) Chain (B) Position (C) Functional (D) Ring chain isomerism

Key Concepts - 2

1 Diethyl amine and methyl propyl amine are metamers justify your answer
2 Write down the possible isomers of C4H9Br and classify them as primary, secondary (or) tertiary
alkyl bromides?
3 C4H10O can show metamerism, functional isomerism position isomerism justify the statement.
4 There are four amides with the formula C3H7NO. Write their structure.
5 A tertiary alcohol with formula C4H10O. Write the structure.
6 A secondary alcohol with C3H8O. Write the structure.
7 Four esters with formula C4H8O2. Write the structure.
8 Three ketones with formula C5H10O. Write the structure.
9 A ketone with formula C3H6O. Write the structure.
10 A ketone with formula C4H8O. Write the structure.
11 4 aromatic ethers with formula C8H10O. Write the structure.
12 Draw all the isomeric forms of C7H9N with benzene ring.
13 Draw structures of all the nine isomers of C7H16.

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 CH-13 ISOMERISM
14 Draw and name all monobromo derivatives of 2,3-dimethyl pentane.
15 Draw all the possible isomers of the structure C4H8O and classify them into their respective
functional groups.

Key Concepts - 3

1 Tautomerism is distinguished from resonance by:

(a) In tautomerism, an atom changes place but in resonance involves change in -elec-
trons or unshared electron.
(b) Resonance structures are theoretical structures where tautomers are practically exists
at dynamic equilibrium.
(c) Two tautomers have different functional groups but there is same functional group in
all canonical structural of the resonance
(d) All of these

2 Which among the following compounds will show tautomerism:

O
||
(a) CH3–CH=NH (b) CH3– C –CH3 (c) CH3– C= CHD (d) CH3–CH=CHD

CH 3
3 Which among the following compounds will show tautomerism:
(a) 2, 2-dimethyl propanal (b) 2, 2-dimethyl-1-nitropropane
(c) Acetyl acetone (d) Benzophenone

4 Which of the following can show tautomerism ?

O
||

(a) (b) (c) (d)

CH 3 CH3
5 Which of the following can show tautomerism ?

(a) (b)

(c) (d)

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 CH-13 ISOMERISM
I II III
Which of the following statements is (are) true about these compounds :
(a) I is the functional isomer of both II and III
(b) All three are tautomers of each other
(c) both (a) and (b)
(d) Only II and III are tautomers of each other
7 Which of the following can show tautomerism ?
CH2 – CH2 – NO2
(a) (b) (c) HCN (d) all of these

8 Which of the following can show tautomerism ?

(a) (CH3)3 CNO (b) (CH3)2NH (c) R3CNO2 (d) RCH2NO2

9 Which will not show tautomerism ?

O NH2 O OH
Me
NH N NH
(a) (b) (c) (d) NH

NH O NH O NH OH NH OH

10 Which will not show Tautomerism?

CH3

(a) CH3CH2CH2CH2NO2 (b) CH3– CH–CH2NO2

(c) CH3 –CH2CH3 (d) (CH3)3C–NO2

Key Concepts - 4

1 Which will not show Tautomerism?

(a) HO–CH=CH–OH (b) (c) (d)

2 Which of the following compound show tautomerism

C=O
(a) (H3C)2CCl–CH=CH2 (b)
H
(c) (H3C)2C(NO2)–CH=CH–CHO (d) None of these

3 Which is a diad form of tautomerism ?

O O
 
(a) (b) CH3–N=O CH2= N–OH

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 CH-13 ISOMERISM

(c) H–O–C N O=C=NH (d) All of these

4 Which of the following is not an example of tautomeric equilibrium ?

(a) (b)

(c) (d)

5 Which is right tautomer of compound ?

O
||
H 3C  CH  CH  C  CH 3

OH OH
|
(a) H 2 C  CH  CH  C  CH 3 (b) H3C–CH=C=C–CH3 (c) both (d) none of these

6 Enol form is more stable in:

(a) CH3CHO (b) CH3COCH3 (c) CH3COCH2COOC2H3 (d) cyclohexanone

7 Which of the following will lead to maximum enolization?

(a) CH3COCH3 (b) CH3COCH2CHO (c) CH3COCH2COCH3 (d)

8 Which among the following compounds will give maximum enol content in solution:

O O
|| ||
(a) C6H5– C –CH2––CH3 (b) CH3– C –CH2––CH3

O O
|| ||
(c) CH2– C –CH2–CH2–CH3 (d) CH3– C –CH2–COOC2H5

9 Which compound has the maximum enolic content?

(a) HOCH2CH2CH2 OH (b) HO CH2CH2 OH

(c) CH3 CH2 OH (d) CH3CH2 OH

10 The enol form of acetone, after treatment with D2O, gives :

OD O OH OD
| || | |
(a) CH 3 – C  CH 2 (b) CD3 – C – CD3 (c) CH 2  C – CH 2 D (d) CD 2  C – CD 3

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 CH-13 ISOMERISM
ANSWER KEY
Key Concepts - 1
1.B 2.A 3.D 4.A 5.B 6.D
7.C 8.D 9.A 10.C 11.C 12.C
13.C 14.D

Key Concepts - 3

1.D 2.AB 3.C 4.D 5.D 6.C

7.D 8.D 9.D 10.D

Key Concepts - 4

1.D 2.D 3.A 4.A 5.A 6.C

7.D 8.D 9.C 10.B

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 CH-13 ISOMERISM
EXERCISE – 1
SINGLE CHOICE CORRECT TYPE QUESTIONS

1. The compounds C2H5OC2H5 and CH3OCH2CH2CH3 are

(A) chain isomers (B) geometrical isomers
(C) metamers (D) conformational isomers

2. The number of primary, secondary and tertiary amines possible with the molecular formula C3H9N
respectively.
(A) 1, 2, 2 (B) 1, 2, 1 (C) 2, 1, 1 (D) 3, 0, 1

3. C7H7Cl shows how many benzenoid aromatic isomers ?

(A) 4 (B) 3 (C) 5 (D) 6

4. Molecular formula C3H6Br2 can have:

(A) Two gem dibromide (B) Three vic dibromide
(C) Two ter.- dibromo alkane (D) Two sec.-dibromo alkane

Br COOH COOH Br

5. and are

HOOC Br Br COOH
(A) Positional (B) Chain (C) Geometrical (D) Functional

6. Which of the following has incorrect relation

Me
Pr Pr
(A) & identical
Me

Me Et
(B) & positional isomers
Pr Pr
Et Et
(C) & positional isomers
Pr
Pr
Me
Me
Et
(D) & homologues
Pr

COOH
OCOH
7. & functional isomer

OMe OEt
Et
& metamers
Me
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 CH-13 ISOMERISM
CH2 – CH2 – OH CH2 – O – CH3

& metamers

Me – N – Me CH2 – NH – CH3

& functional isomers

(A) TFTF (B) FTTF (C) TTFT (D) TFFT

O O
Cl C—O C—O Cl
8. H and CH3
C=C C=C
H CH3 H H
Shows which type of isomerism
(A) Functional group isomerism (B) Geometrical isomerism
(C) Metamerism (D) Position isomerism

9. The type of isomerism observed in urea molecule is

(A) Chain (B) Position (C) Geometrical (D) Functional

10. How many minimum no. of C-atoms are required for position & geometrical isomerism in alkene?
(A) 4, 3 (B) 4, 4 (C) 3, 4 (D) 3, 3

11. Which of the following cannot be written in an isomeric form?

(A) CH3–CH(OH)–CH2–CH3 (B) CH3–CHO
(C) CH2=CH–Cl (D) Cl–CH2CH2–Cl

12. Given compound shows which type of isomerism

O O
S—O and S—O
O O
(A) Chain isomerism (B) Positional isomerism
(C) Metamerism (D) Functional group isomerism

13. Tautomer in following is Diad system :

O

(A) CH3COCH3 (B) CH3CH2NO2 (C) (D) HCN

14. Which of the following does not show geometrical isomerism?

(A) 1, 2-dichloro-1-pentene (B) 1, 3-dichloro-2-pentene
(C) 1, 1-dichloro-1-pentene (D) 1, 4-dichloro-2-pentene

15. What characteristic is the best common to both cis-2-butene and trans-2-butene?
(A) B.P. (B) Dipole moment
(C) heat of hydrogenation (D) Product of hydrogenation

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 CH-13 ISOMERISM

16. The number of cis-trans isomer possible for the following compound

(A) 2 (B) 4 (C) 6 (D) 8

17. Which of the following have zero dipole moment?

(A) benzene 1,4- diol (B) trans-1,2-dichloro ethene
(C) cis-1,2-dichloro ethene (D) 1,1-dichloro ethene

18. Which of the following will not show geometrical isomerism.

Me Me
(A) (B) (C) Cl (D)
Me

19. Geometrical isomerism is possible in:

(A) isobutene (B) acetone oxime
(C) acetophenone oxime (D) benzophenone oxime

20. How many structural isomers of C5H10 are possible.

(A) 10 (B) 11 (C) 12 (D) 13

21. The number of isomers of dibromoderivative of an alkene (molar mass 186 g mol –1) is
(A) 2 (B) 3 (C) 4 (D) 6

22. Increasing order of stability among the three main conformation (i.e. eclipse, anti, gauche) of
ethylene glycol is :
(A) Eclipse, gauche, anti (B) Gauche, eclipse, anti
(C) Eclipse, anti, gauche (D) Anti, gauche, eclipse

23. How many structural isomeric primary amines are possible for the formula C 4H11N?
(A) 2 (B) 3 (C) 4 (D) 5

24. What statement is correct for Keto-enol tautomerism ?

(A) Tautomersim is catalysed by acid and base.
(B) Tautomers are present in dynamic equilibrium state.
(C) Generally keto form is more stable than enol form.
(D) All

25. Among the following the compounds having the highest enol content :
(A) CH3CHO (B) CH3COCH3
(C) CH  C  CH CHO (D) CH3–CO–CH2–CO2CH3
3 2
||
O

26. Tautomer of following compound is :

O O

C – CH2 – C

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 CH-13 ISOMERISM

(A) C – CH = C (B) C – CH2 – C

O OH OH O

(C) CH – CH = CH (D) C – CH2 – C

OH OH O OH

O OH
|| | HO


27. CH 3  C  CH  Ph (II)
( I)
(I) isomerizes to (II) on addition on small amount of base structure of (II) is
OH OH O OH
| | || |
(A) CH 3  CH — CH  Ph (B) H  C  CH 2  CH  Ph

(C) CH 3  CH  C  Ph (D) CH 3  C — C  Ph
| || || ||
OH O O O

28. Which of the following can tautomerise.

O O

(A) CD 3  C  Ph (B) (C) (D) All

|| N
O H

29. Tautomer of which of the following can show geometrical isomerism

(A) CH3–CHO (B) CH3CH2–CHO

O

(C) (CH3)2CH–CH=O (D)

30. Decreasing order of enol content of the following compound in liquid phase

O O O O
|| || || ||
(a) CH 3  C  CH 2  C  O  Et (b) CH 3  C  CH 2  C  CH 3

O O O
|| ||
(c) Ph  C  CH 2  C  Ph (d)

(A) a > b > c > d (B) c > b > a > d (C) c > b > d > a (D) b > c > a > d

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 CH-13 ISOMERISM
31. The compounds C2H5OC2H5 and CH3OCH2CH2CH3 are
(A) chain isomers (B) geometrical isomers
(C) metamers (D) conformational isomers

32. Molecular formula C5H10O can have :

(A) 6-Aldehyde, 4-Ketone (B) 5-Aldehyde, 3-Ketone
(C) 4-Aldehyde, 3-Ketone (D) 5-Aldehyde, 2-Ketone

33. The number of primary, secondary and tertiary amines possible with the molecular formula C3H9N
respectively.
(A) 1, 2, 2 (B) 1, 2, 1 (C) 2, 1, 1 (D) 3, 0, 1

34. C7H7Cl shows how many benzenoid aromatic isomers ?

(A) 4 (B) 3 (C) 5 (D) 6

35. Molecular formula C3H6Br2 can have:

(A) Two gem dibromide (B) One vic dibromide
(C) Two ter.- dibromo alkane (D) Two sec.-dibromo alkane

Br COOH COOH Br

36. and are

HOOC Br Br COOH
(A) Positional (B) Chain (C) Geometrical (D) Functional

37. Which of the following has incorrect relation

Me
Pr Pr
(A) & identical
Me

Me Et
(B) & positional isomers
Pr Pr
Et Et
(C) & positional isomers
Pr
Pr
Me
Me
Et
(D) & homologues
Pr

COOH
OCOH
38 & functional isomer

OMe OEt
Et
& metamers
Me
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 CH-13 ISOMERISM
CH2 – CH2 – OH CH2 – O – CH3

& metamers

Me – N – Me CH2 – NH – CH3

& functional isomers

(A) TFTF (B) FTTF (C) TTFT (D) TFFT

O O
Cl C—O C—O Cl
39 H and CH3
C=C C=C
H CH3 H H
Shows which type of isomerism
(A) Functional group isomerism (B) Geometrical isomerism
(C) Metamerism (D) Position isomerism

40 The type of isomerism observed in urea molecule is

(A) Chain (B) Position (C) Geometrical (D) Functional

41 How many minimum no. of C-atoms are required for position & geometrical isomerism in alkene?
(A) 4, 3 (B) 4, 4 (C) 3, 4 (D) 3, 3

42 How many structural formula are possible when one of the hydrogen is replaced by a chlorine
atom in anthracene?
(A) 3 (B) 7 (C) 4 (D) 6

43 Which of the following cannot be written in an isomeric form?

(A) CH3–CH(OH)–CH2–CH3 (B) CH3–CHO
(C) CH2=CH–Cl (D) Cl–CH2CH2–Cl

44 Only two isomeric monochloro derivatives are possible for (excluding stereo)
(A) n-butane (B) 2, 2-dimethylpentane (C) benzene (D) neopentane

45 Given compound shows which type of isomerism

O O
S—O and S—O
O O
(A) Chain isomerism (B) Positional isomerism
(C) Metamerism (D) Functional group isomerism

46 Which of the following is not the correct relationship

Me Me Me
Me Me

Me Me
O – Me O–Et
OH OH
I II III IV
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 CH-13 ISOMERISM
(A) II & IV are metamer (B) I & II are functional isomer
(C) I & III are chain isomer (D) I and IV are positional isomer

47 Which of the following does not show geometrical isomerism?

(A) 1, 2-dichloro-1-pentene (B) 1, 3-dichloro-2-pentene
(C) 1, 1-dichloro-1-pentene (D) 1, 4-dichloro-2-pentene

48 What characteristic is the best common to both cis-2-butene and trans-2-butene?

(A) B.P. (B) Dipole moment
(C) heat of hydrogenation (D) Product of hydrogenation

49 The number of cis-trans isomer possible for the following compound

(A) 2 (B) 4 (C) 6 (D) 8

50 Which of the following have zero dipole moment?

(A) 1,2-dichloro ethene (B) trans-1,2-dichloro ethene
(C) cis-1,2-dichloro ethene (D) 1,1-dichloro ethene

51 Which of the following will not show geometrical isomerism.

Me Me
(A) (B) (C) Cl (D)
Me

52 Geometrical isomerism is possible in:

(A) isobutene (B) acetone oxime
(C) acetophenone oxime (D) benzophenone oxime
53 The number of isomers of C5H10 is
(A) 10 (B) 11 (C) 12 (D) 13

54 Which of the following have asymmetric carbon atom?

C l Br H Cl H Cl H H
| | | | | | | |
(A) H  C  C  H (B) H  C  C  C l (C) H  C  C  H (D) H  C  C  CH 3
| | | | | | | |
H H H H H H Br OH

55 The number of isomers of dibromoderivative of an alkene (molar mass 186 g mol –1) is
(A) 2 (B) 3 (C) 4 (D) 6

56 Meso-tartaric acid and d-tartaric acid are

(A) positional isomers (B) enantiomers (C) diastereomers (D) racemic mixture

57 The number of isomers of C3H5Br3 is

(A) 4 (B) 5 (C) 6 (D) 7

58 The number of optically active compounds in the isomers of C 4H9Br is

(A) 1 (B) 2 (C) 3 (D) 4

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 CH-13 ISOMERISM

59

The compound with the above configuration is called:

(A) (2S, 3S)-2-chloro-3-hydroxypentane (B) (2S, 3R)-2-chloro-3-hydroxypentane
(C) (2R, 3R)-2-chloro-3-hydroxypentane (D) (2R, 3S)-2-chloro-3-hydroxypentane

60 The full name of the compound is

(A) (2R,3R)-3-chloro-2-pentanol (B) (2R,3S)-3-chloro-2-pentanol

(C) (2S,3R)-3-chloro-2-pentanol (D) (2S,3S)-3-chloro-2-pentanol

61 The structure of (2R, 3R)C2H5CH(CH3)CH(D)CH2D is

(A) (B) (C) (D)

62 The structure of (2R, 3S)C2H5CH(CH3)CH(D)CH2D is

(A) (B) (C) (D)

63 How many stereoisomers can exist for the following acid

H  C(OH ).CO 2 H
|
H  C.CO 2 H
|
H  C(OH ).CO 2 H
(A) Two (B) Four (C) Eight (D) Sixteen

64 How many stereoisomers of the following molecule are possible?

HOOC.CH=C=CH.COOH
(A) two optical isomers (B) two geometrical isomers
(C)two optical and two geometrical isomers (D) None

65 The structures shown here are related as being:

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 CH-13 ISOMERISM
(I) (II)
(A) confermers (B) enantiomers
(C) geometrical isomers (D) diastereoisomers

66 Observe the given compounds and answer the following questions.

(i) Which of the above formulae represent identical compounds?

(A) I and II (B) I and IV (C) II and IV (D) III and IV

(ii) Which of the above compounds are enantiomers?

(A) II and III (B) III and IV (C) III and V (D) I and V
67 Which species exhibits a plane of symmetry?

(A) (B)

(C) (D)

68 Increasing order of stability among the three main conformation (i.e. eclipse, anti, gauche) of
ethylene glycol is :
(A) Eclipse, gauche, anti (B) Gauche, eclipse, anti
(C) Eclipse, anti, gauche (D) Anti, gauche, eclipse

69 How many primary amines are possible for the formula C4H11N?
(A) 2 (B) 3 (C) 4 (D) 5

70 Number of possible 3D-isomers of glucose are

(A) 10 (B) 14 (C) 16 (D) 20

71 The total number of isomeric optically active monochloro isopentanes is:

(A) two (B) three (C) four (D) one

72 On chlorination of propane number of products of the formula C3H6Cl2 is

(A) 3 (B) 4 (C) 5 (D) 6

73 The number of optically active isomers observed in 2,3-dichlorobutane is:

(A) 0 (B) 2 (C) 3 (D) 4

74 What observed rotation is expected when a 1.5 M solution of (R)-2-butanol is mixed with an equal
volume of a 0.75 M solution of racemic 2-butanol and the resulting solution is analysed in a sample
container that is 1 dm long? The specific rotation of (R)-2-butanol is –13.9°ml gm–1dm–1.
(A) +0.77° (B) –0.77° (C) +0.35° (D) –0.35°

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 CH-13 ISOMERISM

75 The two compounds given below are

(A) enantiomers (B) identical (C) optically inactive (D) diastereomers

76 A pure sample of 2-chlorobutane shows rotation of PPL by 30° in standard conditions. When
above sample is made impure by mixing its opposite form, so that the composition of the mixture
becomes 87.5% d-form and 12.5% l-form, then what will be the observed rotation for the mixture.
(A) –22.5° (B) +22.5° (C) +7.5° (D) –7.5°

77 When an optically active compound is placed in a 10 dm tube is present 20 gm in a 200 ml

solution rotates the PPL by 30°. Calculate the angle of rotation & specific angle of rotation if above
solution is diluted to 1 Litre.
(A) 16° & 36° (B) 6° & 30° (C) 3° & 30° (D) 6° & 36°

78 Which of the following will not show optical isomerism.

(A) Cl–CH=C=C=CH–Cl (B) Cl–CH=C=C=C=CH–Cl

(C) (D)

79 The R/S configuration of these compounds are respectively.

HO H
CF3 H NH2 H CH3
HS CHO
COOH
(A) R,R,R (B) R,S,R (C) R,S,S (D) S,S,S

80 Which of the following combinations amongst the four Fischer projections represents the same
absolute configurations?

(A) (II) and (III) (B) (I) and (IV) (C) (II) and (IV)(D) (III) and (IV)

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 CH-13 ISOMERISM
EXERCISE - 2
MULTIPLE CHOICE(S) CORRECT TYPE QUESTIONS
1 In which of the following has minimum torsional strain and minimum Vander waal strain.
CH3 CH3
CH3 CH3 CH3
H H H CH3
CH3

CH3 H H H
H CH CH3 H CH3
CH3 3 CH3
CH3 CH3 CH3
I II III IV
(A) I (B) II (C) III (D) IV
2 The IUPAC name of the compound :

(A) (2E, 4E, 6Z)-octa-2,4,6-triene (B) (2E, 4E, 6E)-octa-2,4,6-triene

(C) (2Z, 4E, 6Z)-octa-2,4,6-triene (D) (2Z, 4Z, 6Z)-octa-2,4,6-triene
3 Which of the following have zero dipole moment?
(A) p-Dichlorobenzene (B) Benzene-1, 4-diol
(C) Fumaric acid (D) Maleic acid
4 Which of the following statements is/are not correct?
(A) Metamerism belongs to the category of structural isomerism
(B) Tautomeric structures are the resonating structures of a molecule
(C) Keto form is always more stable than the enol form
(D) Geometrical isomerism is shown only by alkenes
5 Which compound show tautomerism:
O
OH N OH

(A) (B) (C) (D) None of these

6 Tautomerism form of this compound is/are:

N=O
OH
HO OH

HO OH
OH
O O
HO O HO OH
(A) (B)
HO OH O O
O OH
O
O O
(C) (D) All of these
HO OH
OH
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 CH-13 ISOMERISM
7 Which of the following is not the correct relationship
Me Me Me
Me Me

Me Me
O – Me O–Me
OH OH
I II III IV
(A) II & IV are metamer (B) I & II are functional isomer
(C) I & III are chain isomer (D) I and IV are positional isomer

8 Which of the following compounds have higher enolic content than Keto content:
O O O
|| || O
(A) CH 3  C  C  CH 3 (B)

O O
O
(C) (D)

9 In which of the following pairs first will have higher enol content than second :

(A) & (B) &

(C) & (D) &

10. Which of the following molecules is/are identical with that represented by

(A) (B) (C) (D)

11. In which of the following has minimum torsional strain and minimum Vander waal strain.
CH3 CH3
CH3 CH3 CH3
H H H CH3
CH3

CH3 H H H
H CH CH3 H CH3
CH3 3 CH3
CH3 CH3 CH3
I II III IV
(A) I (B) II (C) III (D) IV

12.
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 CH-13 ISOMERISM

(A) (2E, 4E, 6Z)-octa-2,4,6-triene (B) (2E, 4E, 6E)-octa-2,4,6-triene

(C) (2Z, 4E, 6Z)-octa-2,4,6-triene (D) (2Z, 4Z, 6Z)-octa-2,4,6-triene

13. Which of the following have zero dipole moment?

(A) p-Dichlorobenzene (B) Benzene-1, 4-diol
(C) Fumaric acid (D) Maleic acid

14. Which of the following will show optical isomerism as well as geometrical isomerism.

(A) (B) (C) (D)

15. Which of the following statements is/are not correct?

(A) Metamerism belongs to the category of structural isomerism
(B) Tautomeric structures are the resonating structures of a molecule
(C) Keto form is always more stable than the enol form
(D) Geometrical isomerism is shown only by alkenes
16. Which of the following statements is/are correct?
(A) A meso compound has chiral centres but exhibits no optical activity
(B) A meso compound has no chiral centres and thus are optically inactive.
(C) A meso compound has molecules which are superimposable on their mirror images even
though they contain chiral centres
(D) A meso compound is optically inactive because the rotation caused by any molecule is
cancelled by an equal and opposite rotation caused by another molecule that is the mirror image
of the first.

17. Which of the following statements is/are not correct for D-(+) glyceraldehyde?
(A) The symbol D indicates the dextrorotatory nature of the compound
(B) The sign (+) indicates the dextrorotatory nature of the compound
(C) The symbol D indicates that hydrogen atom lies left to the chiral centre in the Fischer projection
diagram
(D) The symbol D indicates that hydrogen atom lies right to the chiral centre in the Fischer
projection diagram

18. Select the optically inactive compound among the following :

NH H3C COOH
(A) HN (B) H3C COOH

H3C CH3 HN NH
(C) HOOC COOH (D) OC CO

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 CH-13 ISOMERISM
19. The S-ibuprofen is responsible for its pain reliveing property. Which one of the structure shown is
S-ibuprofen.
O
Me C–OH
C Me H
(A) Me (B)
CH3 Me C
H C – OH
CH3 O
CH3 O
Me ||
Me C – OH
Me C H
(C) (D) Me C H
C – OH
O CH3

20. Which of the following operations on the Fischer formula does not change its absolute

configuration?
(A) Exchanging groups across the horizontal bond
(B) Exchanging groups across the vertical bond
(C) Exchanging groups across the horizontal bond and also across the vertical bond
(D) Exchanging a vertical and horizontal group

21. Which of the following statements for a meso compound is/are correct?
(A) The meso compound has either a plane or a centre of symmetry
(B) The meso compound has at least one pair of similar stereocenters
(C) The meso compound is achiral
(D) The meso compound is formed when equal amounts of two enantiomers are mixed

22. Which of the following states are correct:

(A) Any chiral compound with a single asymmetric carbon must have a positive optical rotation if
the compound has the R configuration
(B) If a structure has no plane of symmetry it is chiral
(C) All asymmetric carbons are stereocentres.
(D) Alcohol and ether are functional iosmers

23. Which of the following pairs of compound is/are identical?

(A) (B)

(C) (D)

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 CH-13 ISOMERISM
24. Which of the following compounds are optically active?
(A) CH3.CHOH.CH2.CH3 (B) H2C=CH.CH2.CH=CH2
HOOC NO2

(C) (D)
NO2 COOH

25. Which of the following pairs can be resolved?

(A) (B)

(C) (D)

26. Which of the following are correct representation of L–amino acids

(A) (B)

(C) (D)

27. Which of the following are D sugars:

(A) (B) (C) (D)

28. Which out the following are Non-resolvable.

(A) (B) (C) (D)

29. Which out of the following are resolvable.

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 CH-13 ISOMERISM

(A) (B) (C) (D)

30. Concider the following structure and pick by the right statement :

H O
NH2 C
F OH
C C
H CH2OCH3
H CH2OCH3
CH3 OH III
I II
(A) I and II have R-configuration (B) I and III have R-configuration
(C) only III has S-configuration (D) I and III have S-configuration

31. Which of the following is a 'threo' isomer?

CHO CH3 COOH

COOH
H OH Br H H Cl
H NH2
(A) H OH (B) H (C) H OH (D)
OH H OH
CH2OH CH3 CH3
CH3

EXERCISE-3
COMPREHENSION BASED AND MATRIX MATCH TYPE QUESTIONS

Paragraph for Question Nos. 1 to 3

S(+) Mono Sodium Glutamate (MSG) is a flavour enhancer used in many foods. Fast foods often
contain substantial amount of MSG and is widely used in Chinese food. If one mole of above
MSG was placed in 845 ml solution and passed through 200 mm tube, the observed rotation was
found to be
+ 9.6°.
+
COO¯Na
¯OOC—CH2—CH2—C

NH3 H

MSG
1. Find out the specific rotation of (–) MSG:
(A) + 24° (B) + 56.8° (C) – 48° (D) None of these

2. Find out the approximate percentage composition of (–) MSG in a mixture containing (+) MSG
and (–) MSG whose specific optical rotation is –20°.
(A) 83.3 % (B) 16.7 % (C) 91.6 % (D) 74 %

3. If 33.8 g of (+) MSG was put in 338 ml solution and was mixed with 16.9 g of (–) MSG put in 169

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 CH-13 ISOMERISM
ml solution and the final solution was passed through 400 mm tube. Find out observed rotation of
the final solution
(A) + 1.6° (B) + 4.8° (C) + 3.2° (D) None of these

4. Match column-I with column-II :

Column I Column II
Compound Number of optically active isomer
(A) Unsymmetrical compound with ‘n’ chiral carbon (P) 2 n–1
(B) Symmetrical molecule with ‘n’ chiral carbon when n is even (Q) 2n–1 – 2n–1/2
(C) Symmetrical molecule with ‘n’ chiral carbon when n is odd (R) 2n

5. Match the column :

Column-I Column-II
CH3 H
H CH2OH H3C CH2 NH2
(A) and (P) Structural
NH2 OH
CH3 Cl
H Cl H CH3
(B) and (Q) Identical
Et Et
CH3 H
H H3C
OH Et
(C) and (R) Enantiomers
Et OH
H3C2 H3C2
(D) and (S) Diastereomers
OH H H OH

6. Match List-I, List-II & List-III :

List-I List-II List-III
CH3 H
CH3
Br H
H HO C–C H
(a) HO (1) (i) (2R, 3R)
CH3 CH3 Br

CH3 H
CH3
HO H
Br C–C OH
(b) Br H (2) (ii) (2S,3S)
CH3 H CH3

CH3 H
CH3
H OH
C–C
(c) Br H (3) HO Br
(iii) (2S,3R)
CH3
CH3 H

CH3 H
CH3
HO H
Br C–C OH
(d) H Br (4) (iv) (2R, 3S)
CH3
CH3 H

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 CH-13 ISOMERISM
7. Match Column I with Column II :

Column I Column II
O O
|| ||
(A) CH 3  C  O  C3H 7 & Et  C  O  Et (P) Enantiomer

(B) & (Q) Positional isomers

(C) & (R) Metamers

(D) & (S) Tautomers

8. Match the Column :

Column I Column II
COOH COOH
H OH H OH
;
(a) A pair of metamer (i) HO H H OH
COOH COOH
(b) tautomerism (ii) CH3OC3H7 ; C2H5OC2H5
CH3 CH3
H OH ; HO H
(c) A pair of geometrical isomer (iii)
COOH COOH
CH3 CH3 H3 C H
(d) A pair of distereomers (iv)
C=C ; C=C
H H H CH3
O
||
(e) A pair of optical isomer (v) CH 3CH 2 CH 2 CH ; CH3CH2CH=CH–OH

9. Match Column I with Column II :

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 CH-13 ISOMERISM

Column I Column II
O O
|| ||
(A) CH 3  C  O  C3H 7 & Et  C  O  Et (P) Chain isomer

(B) & (Q) Positional isomers

(C) & (R) Metamers

(D) CH 3  CH  O  CH 3 & CH3–CH2–CH2–O–CH3 (S) Tautomers

|
CH 3

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 CH-13 ISOMERISM
EXERCISE – 4
SUBJECTIVE TYPE QUESTIONS

1 How many benzenoid isomer are possible for cresol.

2 Find out the total number of cyclic structural isomers of C 6H12.

3 How many pair(s) of geometrical isomers are possible with C6H12 (only in open chain structures)

4 Calculate the number of Benzenoid isomers possible for C 6H3ClBrI.

5 Calculate the total number of structural isomers of 3°-amines for the molecular formula C 6H15N
are?

6 How many cyclopentane structures (excluding stereo isomer) are possible for C 7H14.

2H
7 X 
2 
Pt

Find out structures of X.

8 Calculate the total number of cyclic isomeric carbonyl compounds of molecular formula C 5H8O
which can't show geometrical isomerism.

9 Assign E & Z configuration?

O O
O
O
(I) (II)
O
Z E
CH2CH2CH3
Ph
(III) CH – CH3 (IV) Cl
|
CH3
F
| NC CH = CH2
C–C–C Br
(V) F (VI)
HOOC CHO
C–C–C Cl
Z
C  CH O
HO
CH3 O O

(VII) OHC C – CH3 (VIII) O

| O
CH3 O
18
Me OMe OH
H
(IX) (X) 16
Et O¯ Li
+
D OH

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 CH-13 ISOMERISM
CH3
|
CH – CH2 – CH3
Me F
C  CH
(XI) (XII)
Cl Me CH3
H

10 Mention the specific type of isomerism exhibited by each of the following pairs:
(a) 1,2-dichloro ethane and 1,1-dichloro ethane
(b) Propanoic acid and methyl acetate
(c) Methyl acetate and ethyl formate
(d) o-Nitrophenol and P-nitrophenol
(e) Anisole and o-cresol
(f) Phenol and Cyclohexa-2,4-dien-1-one

11 Draw the two chair conformers of each compound and indicate which conformer is more stable.
(a) cis-1-ethyl-3-methylcyclohexane (b) trans-1-ethyl-2-isopropylcyclohexane
(c) trans-1-ethyl-2-methylcyclohexane (d) trans-1-ethyl-3-methylcyclohexane
(e) cis-1-ethyl-3- isopropylcyclohexane (f) cis-1-ethyl-4-isopropylcyclohexane

12 Draw the most stable conformer of N-methylpiperidine.

13 Considering rotation about the C-3 – C-4 bond of 2-methylhexane:

(a) Draw the Newman projection of the most stable conformer.
(b) Draw the Newman projection of the least stable conformer.

14 Determine whether each of the following compounds is a cis isomer or a trans isomer.

(a) (b)

(c) (d)

(e) (f)

15 Write down all the benzenoid isomers of formula C 7H7O2N. What type of isomerism they show?

16 Assign the priority order number to the following atoms or groups.

(a) –CHO, –CH2OH, –CH3 , –OH (b) –Ph, –CH(Me)2, –H, –NH2

(c) –COOH, –Ph , –CHO, –CH = CH2 (d) –CH(Me)2, –CH=CH2, –CCH, –Ph

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 CH-13 ISOMERISM

(e) –CH3, –CH2Br, –CH2OH, –CH3Cl (f) –H, –N (Me)2, –Me, –OMe

(g) –CH = CH2, –Me, – Ph, –Et

(h) –CH2–CH2–Br, –Cl, –CH2–CH2–CH2–Br, (Me)2CH–

(i) –Cl, –Br, –I, –NH2 (j) NH2 , NO2 , CH2NH2 , CN

17 In each of the following pairs which is more stable :

(a) l (b) l

(c) l (d) l

(e) l

18 In each of the following pairs which is more stable :

(a) (b)

(c) l (d) l

(e) l

19 In each of the following pairs which will have less enol content :

(a) and (b) and

(c) and (d) and

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 CH-13 ISOMERISM
(e) CH 2  CHO and CH 3  CHO
|
Cl
20 In each of the following pairs which will have less enol content :

(a) and (b) and

21 In each of the following sets of compounds write the decreasing order of % enol content.

(a)

(b)

22 In each of the following sets of compounds write the decreasing order of % enol content.

(a)

(b)

23 In each of the following sets of compounds write the decreasing order of % enol content.

24

Among these give ease of enolization.

25 % enol content of acetylacetone in following solvents is found as :
Solvent % enol content
H2 O 15
Liquid state 76
hexane 92
gas phase 92
Explain the observation.
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 CH-13 ISOMERISM

26

Explain the observation.

27 Decreasing order of enol content of the following. (along with proper explanation).

(a) (b) (c) (d)

(e)

28 Ph  CH  CHO
|
OH
(A)
(A), (B) and (C) are structural isomers and isomerization is effectively carried out by trace of
base. Give structure of (B) and (C) and also write base catalysed mechanism for this
interconversion.

29 Calculate the total number of open chain isomeric carbonyl compounds of molecular formula
C5H8O which can't show geometrical isomerism.

30 How many isomer are possible for cresol.

31 Calculate the total number of stereoisomers in the following compounds.

(I) (II) (III)

32 Find out the total number of cyclic isomers of C6H12 which are optically active?

33 How many pair(s) of geometrical isomers are possible with C6H12 (only in open chain structures)

34 Calculate the number of Benzenoid isomers possible for C 6H3ClBrI.

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 CH-13 ISOMERISM

35 Calculate the total number of structural isomers of 3°-amines for the molecular formula C 6H15N
are?

36 Calculate the number of chiral center in the molecule Ethyl 2,2-dibromo-4-ethyl-6-methoxy

cyclohexane carboxylate.

37 How many monochlorinated products of methyl cyclohexane are optically active.

38 How many cyclopentane structures (including stereo) are possible for C 7H14.

2H
39 X 
2 
Pt

Find out structural isomers of X.

40 How many enantiomers are possible on monochlorination of isopentane.

41(a) Calculate the total number of cyclic isomeric carbonyl compounds of molecular formula C 5H8O
which can't show geometrical isomerism.
(b) Calculate the total number of open chain isomeric carbonyl compounds of molecular formula
C5H8O which can't show geometrical isomerism.

42 Calculate the total number of chiral carbon atoms in progesterone ( a steroid).

(i) H H (ii)
O
HO
(Progesterone)
43 (a) The number of cyclic stereoisomers (excluding optical) for the molecular formula : C3H3Cl BrI
(b) Minimum number of carbon atoms required for an alkane to show any kind of isomerism.

44 Assign E & Z configuration?

O O
O
O
(I) (II)
O
Z E
CH2CH2CH3
Ph
(III) CH – CH3 (IV) Cl
|
CH3

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 CH-13 ISOMERISM
F
| NC CH = CH2
C–C–C Br
(V) F (VI)
HOOC CHO
C–C–C Cl
Z

C  CH O
HO
CH3 O O

(VII) OHC C – CH3 (VIII) O

| O
CH3 O
18
Me OMe OH
H
(IX) (X) 16
Et O¯ Li
+
D OH

CH3
|
CH – CH2 – CH3
Me F
C  CH
(XI) (XII)
Cl Me CH3
H

45 Write the structure of:

(i) (E) penta-1,3-diene (ii) (2Z, 4E)hexa-2,4-diene
(iii) (2E, 4E)-3-ethylhexa-2,4-diene (iv) (R)-2-Bromopentane
(v) (S)-3-bromo-3-chlorohexane (vi) (2S, 3R)-2,3-dibromobutane

46 In what stereoisomeric forms would you expect the following compounds to exist?
(a) EtCH(CO2H)Me (b) MeCH(CO2Et)CO2H

(c) (d)

(e) (f) Et(Me)C=C=C(Me)Et

(g) (h)

(i) (j) (k)

47 What are the relationships between the following pairs of isomers?

(a) and (b) and

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 CH-13 ISOMERISM

(c) and

(d) and

(e) and (f) and

(g) and (h) and

(i) and

48 Mention the specific type of isomerism exhibited by each of the following pairs:
(a) 1,2-dichloro ethane and 1,2-dichloro ethane
(b) Propanoic acid and methyl acetate
(c) Methyl acetate and ethyl formate
(d) o-Nitrophenol and P-nitrophenol
(e) Anisole and o-cresol
(f) Phenol and Cyclohexa-2,4-dien-1-one

49 With reasons, state whether each of the following compounds I to IX is chiral.

(I) (II) (III)

(IV) (V) (VI) (VII)

50 Draw the two chair conformers of each compound and indicate which conformer is more stable.
(a) cis-1-ethyl-3-methylcyclohexane (b) trans-1-ethyl-2-isopropylcyclohexane
(c) trans-1-ethyl-2-methylcyclohexane (d) trans-1-ethyl-3-methylcyclohexane
(e) cis-1-ethyl-3- isopropylcyclohexane (f) cis-1-ethyl-4-isopropylcyclohexane
51 Draw the most stable conformer of N-methylpiperidine.
52 Considering rotation about the C-3 – C-4 bond of 2-methylhexane:
(a) Draw the Newman projection of the most stable conformer.
(b) Draw the Newman projection of the least stable conformer.

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 CH-13 ISOMERISM

53 Determine whether each of the following compounds is a cis isomer or a trans isomer.

(a) (b)

(c) (d)

(e) (f)

54 Comment on the relationship among the following compounds.

(I) (II) (III) (IV)

55 Calculate the total number of geometrical isomers possible for

Cl
Cl Cl
H CH = CH – CH3
(i) (ii) (iii) C=C=C
Cl Cl Cl CH = CH – CH3
Cl

56 Total number of streoisomers for the following molecule : (including optical)

Et Me

(i) (ii)
CH3 – CH – CH = CH CH = CH – CH – CH3 Me
| |
CH3
COOH
Cl

NH2
N O
O N

(iii) EtO – P N N (iv)

OH
OEt
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 CH-13 ISOMERISM

OH

(v) (vi)

57 How many stereocenter and pseudochirality center present in the following compound?

O
H2 N NH2
O O

58 A 0.1 M solution of an enantiomerically pure chiral compound. D has an observed rotation of

+0.20° in a 1 dm sample container, the molecular mass of the compound is 150.
(a) What is the specific rotation of D ?

(b) What is the observed rotation if this solution of D is diluted with an equal volume of solvent?

(c) What is the observed rotation if this solution is mixed with an equal volume of a solution
that is 0.1 M in L, the enantiomer of D?

(d) What is the specific rotation of D after the dilution described in part (b) ?

(e) What is the specific rotation of L, the enantiomer of D, after the dilution described in part (b)?

(f) What is the observed rotation of 10 ml of a solution that contains 0.01 mole of D and
0.005 mole of L? (Assume a 1 dm path length)

59 Assign the priority order number to the following atoms or groups.

(a) –CHO, –CH2OH, –CH3 , –OH

(b) –Ph, –CH(Me)2, –H, –NH2

(c) –COOH, –Ph , –CHO, –CH = CH2

(d) –CH(Me)2, –CH=CH2, –CCH, –Ph

(e) –CH3, –CH2Br, –CH2OH, –CH3Cl

(f) –H, –N (Me)2, –Me, –OMe

(g) –CH = CH2, –Me, – Ph, –Et

(h) –CH2–CH2–Br, –Cl, –CH2–CH2–CH2–Br, (Me)2CH–

(i) –Cl, –Br, –I, –NH2

(j) NH2 , NO2 , CH2NH2 , CN

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 CH-13 ISOMERISM
ANSWER KEY
EXERCISE-1

1. C 2 C 3 A 4 A 5 A 6 B 7 C
8. C 9 D 10 B 11 C 12 C 13 D 14 C
15. D 16 A 17 B 18 A 19 C 20 A 21 B
22. C 23 C 24 D 25 C 26 A 27 C 28 D
29. B 30 B 31. C 32 B 33 C 34 A 35 A
36 A 37 B 38. C 39 C 40 D 41 B 42 A
43 C 44 A 45. C 46 D 47 C 48 D 49 A
50 B 51 A 52. C 53 D 54 D 55 B 56 C
57 C 58 B 59. A 60 A 61 A 62 B 63 B
64 A 65 D 66. (i) B, (ii) C 67 D 68 C 69 D
70 C 71 C 72 C 73 B 74 B 75 A 76 B
77 B 78 A 79 A 80 C

EXERCISE-2
1 B 2 C 3 A,C 4 B,C,D 5 A,C 6 A,B
7 A,D 8 B,D 9 A,C 10 A,D 11 B 12 C
13 A,C 14 A,C,D 15 B,C,D 16 A,C 17 A,D 18 A,C,D
19 D 20 C 21 A,B,C 22 C,D 23 A 24 A,C,D
25 B,C,D 26 A,C,D 27 A,C,D 28 A,C 29 D 30 A,C
31 B

EXERCISE-3

1. D 2. C 3. C 4. (A) R , (B) P, (C) Q

5. (A) P , (B) R , (C) Q , (D) R 6. (a-4-iii) ; (b-3-iv) ; (c-2-ii) ; (d-1-i)
7. (A) R, (B) Q, (C) S, (D) P 8. (a) ii (b) v (c) iv (d) i (e) iii
9. (A) R, (B) Q, (C) S, (D) Q

EXERCISE-4

1. 5 2. 11 3. 4 4. 10 5. 7 6. 4 7. 7
8. 9 9. Z – I, II, III, VI, VII ; E – IV, V, VIII, IX, X, XI, XII
10. (a) Positional (b) Functional (c) Metamerism (d) Positional (e) Functional (f) Tautomerim

11. Stable are : (a) diequatorial, (b) , (c) (d) ,

(e) , (f)

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 CH-13 ISOMERISM

12.

H H Et

13. (a) (b)

H H
H H H
Et H
14. (a) cis (b) cis (c) cis (d) trans (e) trans (f) trans

15. Position isomers, Functional isomers, Tautomers isomers, Geometrical isomers

CH3

NO2

16. (a) 4,1,2,3 (b) 4,1,2,3 (c) 1,3,2,4 (d) 4,3,2,1 (e) 2,4,3,1 (f) 4,2,3,1 (g) 3,1,4,2 (h) 2,4,1,3
(i) 3,2,1,4 (j) 2, 1, 4, 3

17. (a) 1; (b) 1; (c) 1; (d) 1; (e) 1 18. (a) 2; (b) 2; (c) 1; (d) 2; (e) 1

19. (a) 2; (b) 1; (c) 2; (d) 1; (e) 2 20. (a) 2; (b) 2

21. (a) 3>1>2; (b) 4>2>1>3 22 (a) 4 > 1 > 3 > 2 ; (b) 3>1>4>2

23 3>4>2>1 24 3>1>2

25 > > > >

(a) (b) (c) (d) (e)

(a) Tightly on stable keto due to repulsion between – CO groups has 100 % enol. >
(b) Active 'H' atom / Acidic 'H' atom so has more enolic content (enol stabilise by resonance & Intra
molecular H–bonding) >
(c) Enolic contents decreases with introduction of e– donator group which causes repulsion in enolic
form .
(d) Due to ester group acidic structure of active H decreases & C=C of enol undergoese cross
resosnace >

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 CH-13 ISOMERISM
(e) Lowest enolic content because is more stable than Bond

26. Subjective

27. c>a>d>b>e

28 Ph  C  CH Ph  C  CH 2
| | || |
OH OH O OH
( B) ( C)
(Mechanism)

Ph  CH  CH 
 Ph  C  CH Ph  C  CH
| || | | | |
OH O OH O  OH OH
( B)


Ph  C  CH 2 Ph  C  CH
|| | || |
O OH O OH
(C )

29 8

30 5 31 (I) 4, (II) 3, (III) 4 32 8

33 10 34 7 35 8

36 8 37 7 38 4

39. Subjective 40. 4

41 (a) 8, (b) 8

42 (i) 6, (ii) 8 43 (a) 4, (b) 4

44 (Z) – I, II, III, VI, VII ; (E)– IV, V, VIII, IX, X, XI, XII

45 (i) (ii)

Et
Et
C2H5
H Br
(iii) (iv)
CH3

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 CH-13 ISOMERISM
C3H7 CH3
H Br
Cl Br
(v) (vi) H Br
C2H5 CH3

46 Optical : a,b,c,d,f,g,i,j,k ; Geometrical isomer : c,g,j ; None : e,h,

47 (a) Enantiomers, (b) Enantiomers, (c) Geometrical isomers & Diastereomers, (d) Positional,
(e) Optical (Diastereomers), (f) Diastereomers, (g) Enantiomers, (h) Identical, (i) Geometrical
isomers (Diastereomers)

48 (a) Positional (b) Functional (c) Metamerism (d) Positional (e) Functional (f) Tautomerism

49 achiral : I, III, IV; chiral : II,V, VI, VII

50 Stable are : (a) diequatorial, (b) , (c) (d) ,

(e) , (f)

H H Et

51 52 (a) (b)
H H
H H H
Et H

53 (a) cis (b) cis (c) cis (d) trans (e) trans (f) trans

54 II, III & IV are Identical; I is Enantiomer of these.

55 (i) 16 (ii) 8 (iii) 4

56 (i) 25 , (ii) 24 , (iii) 2 , (iv) 4 , (v) 3, (vi) 8

57 3,1

58 (a) + 13.3 ; (b) 0.10 ; (c) zero ; (d) unchanged ; (e) unchanged ; (f) 1

59 (a) 4,1,2,3 (b) 4,1,2,3 (c) 1,3,2,4 (d) 4,3,2,1 (e) 2,4,3,1 (f) 4,2,3,1 (g) 3,1,4,2 (h) 2,1,4,3
(i) 3,2,1,4 (j) 2, 1, 4, 3

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 CH-14 HYDROCARBONS
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CHAPTER-14
HYDROCARBONS

EXERCISE – 1
SINGLE CHOICE CORRECT TYPE QUESTIONS
Properties of alkanes:-
1. A hydrocarbon with formula C8H18 gives one monochloro derivative) The hydrocarbon is
(A) n-octane (B) 2-methylheptane
(C) 2, 2, 4-trimethyl pentane (D) 2, 2, 3, 3-tetramethyl butane)

2. An organic compound A (C5H8) on hydrogenation gives compound B(C5H12) compound A

on ozonolysis give methanal and 2-ketopropanal) The compound (A) is

CH3 CH3
H2C H2C
(A) (B)
H2C HC

CH2
H3C
H3C
(C) (D)
H3C CH3
H3C

OH

3. In the dehydration of,

The product formed are

CH2 CH3

(I) (II) (III)

(A) Only I (B) Only II (C) Only III (D) I, II and III

4. Hydroboration oxidation and acid hydration will not give the same products in case of

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(A) (B)

(C) CH2 = CH2 (D) CH3CH = CH —CH3

5. The major product obtained in the dehydrohalogenation of neopentyl bromide with alcoholic
KOH is
(A) 2-methylbut-1-ene (B) 2, 2-Dimethyl but-1-ene
(C) 2-methyl but-2-ene (D) But-2-ene

6. The addition of Br2 to trans-But-2-ene produces

(A) (+) 2, 3-dibromobutane (B) (–) 2, 3-dibromobutane
(C) Racemic -2, 3-dibromobutane (D) meso-2, 3-dibromobutane

7. In the reaction sequence

O3 / H2O 
A   B   2CH3COOH  2CO 2
the reactant A is

(A) (B) (C) (D)

CH3
8. CH2  HBr 
A (Major product), A is
H3C

CH3
CH3
CH3
(A) H3C (B)
H3C Br
Br

Br
H3C
(C) (D) None is correct
CH3 CH3

H
CH3
9. H3C 
aq. alkaline KMnO 4
A
H

Which of the following is true about this reaction?

(A) A is meso-2, 3-butanediol formed by syn addition

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(B) A ismeso-2, 3-butanediol formed by anti addition
(C) A is a racemic mixture of d and l-2, 3-butanediol formed by anti addition)
(D) A is a racemix mixture of d and l-2, 3-butanediol formed by syn addition

Properties of alkynes:-

10. In the reaction


H3O
Ph  C  C  CH3 
HgSO4
 A, A is

O OH
Ph Ph
Ph Ph
O OH
(A) (B) (C) (D)
H3C H3C
H3C H3C

Preparation of alkanes:-
11. A sample of 4)50 mg of unknown alcohol is added to CH3MgBr when 1)68 ml of CH4 at
STP is obtained) The unknown alcohol is
(A) Methanol (B) Ethanol (C) Propan-1-ol (D) Butan-1-ol
12. Which of the following will have least hindered rotation about carbon carbon single bond?
(A) Ethane (B) Ethene
(C) Ethyne (D) Hexachloroethane

Preparation of alkenes:-

13. The major product in the dehydrohalogenation of 2-Bromo-3, 3-dimethyl-butane is

(A) 3, 3-dimethyl but-1-ene (B) 2, 3-dimethylbut-1-ene
(C) 2, 3-dimethyl but-2-ene (D) 4-methylpent-2-ene


i) BH3 / THF H3 O
14. B 
ii) H O /OH
 CH2  A
2 2

A and B are respectively

CH3 CH3
(A) CH2OH, CH2OH (B) ,
OH OH

CH3 CH3
CH2OH , , CH2OH
(C) (D)
OH OH

15. In the following reaction

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 CH-14 HYDROCARBONS
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CH3


H3C 
D2O/D
A
the product (A) is
CH3 CH2

CH3 CH3 CH3

H3C CH2D H3C CH2D
(A) (B)
CH3OD OD

CH3 H CH3
H3C CH3 H3C
(C) (D)
OD D CH3 D OD

16. The olefine, which on ozonolysis give CH3CH2CHO and CH3CHO is

(A) But-1-ene (B) But-2-ene (C) Pent-1-ene (D) Pent-2-ene

17. The intermediate during the addition of HCl to propene in the presence of peroxide would be

   CH3  CH CH2
(A) CH3 CHCH2Cl (B) CH3  CH  CH3 (C) CH3 CH2 CH2 (D) |
Cl

18. 2-methyl pent-2-ene on ozonlysis will give

(A) Propanal only (B) Propanal and ethanal
(C) Propanone & propanal (D) Propan-2-ol and ethanal

Properties of alkynes:-

19. 2-Butyne which treated with lithium in presence of liquid ammonia gives
(A) cis-2-butene (B) trans-2-butene (C) n-butane (D) 1-butyne

20. Which of the following compound on oxidative ozonolysis give malonic acid as only product)
(A) CH2 = CH – CH2 – CH = CH2 (B) CH2 = CH – CH = CH2

(C) (D)

21. In the following sequence of reactions, the product (D) is

HBr HBr alc KOH NaNH2
CH  CH   A   B   C  D
(A) Ethanol (B) Ethyne (C) Ethanal (D) Ethene

22. Which of the following is used for the conversion of 1-methylcyclo-pentene to

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 CH-14 HYDROCARBONS
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CH3

(A) BD3/THF followed by CH3COOH (B) BH3/THF followed by CH3COOD

(C) BD3/THF followed by CH3COOD (D) BH3/THF followed by CD3COOH
dil H2SO4
23. Ph – CH2 – CH = CH2  A , A is

Ph  CH2  CH CH3

(A) Ph—CH2—CH2—CH2—OH (B) |
OH

Ph  CH CH2  CH3

(C) | (D) Ph—CH2—OH
OH
24. The compound 1, 2-butadiene has
(A) only sp-hybridized carbon atoms (B) only sp2-hybridized carbon atoms
(C) both sp & sp2-hybridized carbon atoms (D) sp, sp2 and sp3 hybridized carbon
atoms

25. Acidic hydrogen is present in

(A) ethyne (B) ethane (C) benzene (D) ethane

26. The number of structural and configurational isomers of a bromo compound, C 5H9Br, formed
during the addition of HBr to 2-pentyne respectively :
(A) 1 and 2 (B) 2 and 4 (C) 4 and 2 (D) 2 and 1

27. The compound which has one isopropyl group is

(A) 2, 2, 3, 3 tetramethyl pentane (B) 2, 2 dimethyl pentane
(C) 2, 2, 3-trimetyl pentane (D) 2-methyl pentane

28. The C–H bond distance is longest in

(A) C2H2 (B) C2H4 (C) C2H6 (D) C2H2Br2

29. When cyclohexane is poured on water, it floats, because :

(A) cyclohexane is in boat form (B) cyclohexane is in chair form
(C) cyclohexane is in crown form (D) cyclohexane is less dense than water

30. Which of the following alkanes is not obtained by Wurtz reaction?

(A)Methane (B) Ethane (C)Propane (D) Butane

CH3

31. The alkene that give OH

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 CH-14 HYDROCARBONS
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By the oxymercuration demercuration is

CH3
(A) CH CH2 (B)

CH3 CH3
(C) (D)

CH2 CH2 OH


A

OH

CH2


B

32.
OH


C

A, B & C are respectively

(A) Simple hydration reaction
(B) Hydroboration, acid catalysed hydration oxidation and oxymercuration demercuration
(C) Hydroboration oxidation, oxymercuration demercuration and acid catalysed hydration
(D) Oxymercuration demercuration, hydroboration oxidation and acid catalysed hydration)

33. Which is the most suitable reagent among the following to distinguish compound (III) from
the rest of the compounds
(I) CH3 — C  C —CH3 (II) CH2—CH2—CH2—CH3
(III) CH3—CH2 — C  C H (IV) CH3—CH = CH2
(A) Br2 in CCl4 (B) cold aq) Alk KMnO4
(C) Ammonical AgNO3 solution (D) All of these

H3C H

Br2
 A,
34.
H CH3

Which of the following statement is true?

(A) A is formed by anti addition and is meso
(B) A is formed by syn addition and is meso
(C) A is formed by anti addition and is racemic (D) A is formed by syn addition and is racemic
35. A sample of 1)79 mg of a compound of molar mass 90g mol–1 when treated with CH3MgI
releases 1)34 ml of a gas at STP) The number of active hydrogens in the molecule is

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(A) 1 (B) 2 (C) 3 (D) 4

36. Which one of following has the smallest heat of hydrogenation per mole?
(A) 1-butene (B) trans-2-butene (C) cis-2-butene (D) ethene

37. Which of the following alkane is synthesized from single alkyl halide?

(A) (B)

(C) (D)

38. C6H12(A) has chirality but on hydrogenation A is converted into C6H14(B) in which chirality
disappears) Hence A is
(A) 3-Methyl-1-pentene (B) 2-Methyl-2-pentene
(C) 2, 3-dimethyl-2-buene (D) 3, 3-dimethyl-1-butene

39. C8H18(A) on chlorination forms only one type of C8H17Cl) Hence A is

(A) (B)

(C) (D)

Cl2  H2O
40. CCl3 CH  CH2  A, A is

OH Cl
(A) Cl (B) OH
CCl3 CCl3

CCl3 CCl3 CH2

(C) (D)
Cl Cl OH OH

41. Which of the following alkene has the slowest rate of hydrogenation?

H3C CH3
CH3
CH2 H3C H
H3C CH3
H3C
(I) (II) (III) (IV)

(A) I (B) II (C) III (D) IV

42. In the reaction
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 CH-14 HYDROCARBONS
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CH3

CH2N2
X

The product X is

(A) (B)

CH3

CH3
(C) (D)
CH3

43. The compound ‘A’ decolourise bromine solution and it undergoes catalytic reduction to
give decalin) When treated with warm conc) Potassium permanganate, this compound
give cis-cyclohexane-1, 2-dicharboxylic acid and oxalic acid compound ‘A’ is

(A) (B)

(C) (D)

44. In the following reaction

C6H5 CO3H
CH CH  A

Product A is

O O
O
CH CH
(A) HC CH (B)
O

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 CH-14 HYDROCARBONS
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O O OH
HC CH
(C) (D) CH CH
O
O

45. The number of stereoisomers obtained by the bromination of trans-2-butene is

(A) 1 (B) 2 (C) 3 (D) 4

o
46. CH2 = CH —CH3 
Cl2 , 500 C
A
The product A is

H3C CH CH2 Cl
(A) (B) H2C
Cl Cl

H2C CH2 HC CH CH2

(C) (D)
Cl Cl Cl Cl

47. The reagent(s) for the following conversion,

Br
Br 
?
 H H is/are
(A) alcoholic KOH (B) alcoholic KOH followed by NaNH2
(C) aqueous KOH followed by NaNH2 (D) Zn/CH3OH

BD3 /THF
48. 
H O /OH
A, A is
2 2

CH3
D
(A) OH (B)
OH

CH3
OH
(C) OH (D)
D D

49. 
A

 A can be

(A) conc) H2SO4 (B) alc) KOH (C) Et3N (D) t-BuOK

CH2
50.  
 A, A is
CH2

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(A) (B)

(C) (D)

H3C CH2OH

51. The major product obtained in the acid-catalysed dehydration of is

CH3 CH2
CH3 CH3
CH3 CH2
(A) (B) (C) (D)

Li/NH3 (l)
52. C C C C   X, X is

(A) (B)

(C) (D)

53. The major product formed by the acid catalysed hydration of

CH3
Is

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 CH-14 HYDROCARBONS
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OH
OH OH OH

(A) CH3 (B) CH3 (C) (D)

H3C
CH3


MCPBA
 A,
54.

Product A is

OH OH
(A) OH (B) OH

O OH
(C) (D) OH

light Na/Ether
55. C5H12  Cl2   C5H11Cl  C
(A) (B)

Only one structure of B is possible) The product C is

CH3
CH3CH3
H3C C CH3
C C
(A) CH3 C CH3 (B)
H3C CH3CH3 CH3
CH3

CH3CH3 CH3CH3
C C CH3 H3C C C CH3
(C) (D)
H3C CH3CH3 CH3CH3

Cl
DO

Mg/ether
 
2
 
Na/ether
 A,
56. (1eq)

Br
The product A is

(A) Br Cl (B) D D

(C) Cl D (D) D D

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 CH-14 HYDROCARBONS
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O O

57. O3
C9H14 
Zn/H2 O

(A )

The reactant A is

(A) (B)

(C) (D)


58. CH= CH CH3 
HO/H
2
A(majorproduct), A is

CH2 CH CH3 CH CH2 CH3

(A) (B)
OH OH

CH CH CH3
(C) (D) HO CH CH CH3

OH

59. The reaction

CH3CH CH OH with HBr gives

(A) CH3 CHBrCH2 OH (B) CH3 CH2 CHBr OH

(C) CH3 CHBrCH2 Br (D) CH3 CH2 CHBr Br

EXERCISE - 2
MULTIPLE CHOICE(S) CORRECT TYPE QUESTIONS

C 4 H 6  H2
Pd / Baso 4
 C 4 H8 
O3 H 2 O
 2CH 3COOH
1.
(A) (B)

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Which of the following dosenot gives compounds A & B correctly
(A) CH3—C  C—CH3, CH3—CH = CH —CH3
(B) CH2 = CH—CH = CH2, CH3—CH = CH —CH3
(C) CH3—CH2—C CH, CH3—CH2—CH = CH2

(D) , CH3—CH = CH —CH3

2. Which of the following compounds on reductive ozonolysis give only glyoxal

(A) Ethylene (B) Benzene (C) Toluene (D) Cyclobuta-1, 3-diene

3. Grignard’s reagent gives alkane with

(A) H2O (B) C2H5OH (C) C2H5NH2 (D) CH3—O—CH3

4. The monochlorinated products obtained by the chlorination of isobutene are

(A) n-Butyl chloride (B) Sec) butylchloride
(C) Tert butylchloride (D) Isobutyl chloride
5. Which of the following reduces 2-Butyne into cis-2-butene)
(A) Na/NH3(l) (B) BH3 followed by CH3COOH
(C) H2/Pd-BaSO4 (D) Li/NH3(l)
6. Which of the following reagent bring about the following conversion)

OH

OH

(A) OsO 4/H 2O2 (B) KMnO4/OH– (cold & aq))

(C) Peracids followed by hydrolysis (D) I2 and CH3 COOAg
7. Which of the following reagents can be used for the following conversion

CH3 CH3

(A) NH2NH2, glycol/OH– (B) Zn – Hg/conc) HCl

(C) HI/Red P (D) LiAlH4

CH3CH3

8. A 
HBr
 H3C CH3
Br H
The reactant ‘A’ can be

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CH3 CH3
H3C
CH3
H C
(A) 3 (B) H3C
CH3 CH2 OH

CH3 H3C CH3

(C) H3C (D)

OH CH2 H3C CH3

H3 C CH3 H3C H

H H H CH3
CH3CO3H CH3 CO3H
9.
(A) (C)

H / H2O H / H2O

(B) (D)

Which of the following statements are true?

(A) B is a single compound and is optically inactive
(B) D is a single compound and is optically inactive
(C) B is an equimolar mixture of two enantiomeric compounds
(D) D is an equimolar mixture of two enantiomeric compounds

HgSO 4/H2SO 4
10.
BH3/THF
A B
H2O2/OH

Hg(OAC) 2, H2O
NaBH4

B is identical when A is
(A) CH  CH (B) CH3 – CH  CH
(C) CH3– CH  CH – CH3 (D) CH3 – CH2 – CH  CH
11. Hydroboration oxidation and acid hydration will yield the same product in case of:

(A) (B)

(C) CH2 = CH2 (D) CH3CH = CHCH3

12. Ammonical silver nitrate reacts with
(A) ethyne (B) ethylene
(C) butyne-1 (D) butyne-2

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13. Which of the following compounds will show cis-trans isomerism?

(A) (H3C)2C = CH — CH3 (B) H2C = CCl2
(C) C6H5(H)C = CH — CH3 (D) H3C — CH = CBr(CH3)

14. Which of the following statements are correct:

(A) Hydrogenation of 2-butyne in presence of Na and liquid ammonia yields trans-2-
butene
(B) Hydrogenation of 2-butyne in presence of Lindlar’s catalyst yields cis-2-butene
(C)Hydrogenation of 2-butyne in presence of Pt catalyst gives cis-2-butane
(D) Hydrogenation of 2-butyne in presence of Ni2B catalyst gives cis-2-butane

15. Which of the following statements are correct on the basis of heat of combustion:

(A) Trans-2-hexene has less heat of combustion than 2-methyl-2-pentene

(B) Cis-2-pentene has higher heat of combustion than trans-2-pentene
(C) 1-hexene has higher heat of combustion than trans-2-hexene
(D) 2, 5-dimethyl hexane has higher heat of combustion than octane
16. Which is/are true statements/reactions?
(A) Al4C3 + H2O  CH4 (B) CaC2 + H2O  C2H2
(C) Mg2C3 + H2O  CH3C CH (D) SiC + 4H2O  CH4+ Si(OH)4
17. Which gases are poisonous?
(A) Lewisite (B) Mustard
(C) Phosgene (D) MIC

EXERCISE - 3
COMPREHENSION BASED TYPE QUESTIONS
Comprehension- I
Hydrogenation of alkenes and alkynes takes place in presence of certain catalysts) In
sabatier-senderen’s reaction, the addition of hydrogen takes place in presence of Nickel
catalyst) Controlled hydrogenation of alkyne in presence of Lindlar’s catalyst gives cis-
alkene) Non terminal alkynes are reduced by of Na or Li metal dissolved in liquid NH3) In
this reaction trans alkenes are formed)
1. In which of the following the reaction is most exothermic)

(A) (B)

(C) (D)

2. The product of the following reaction is

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O O

(A) (B)

OH OH

(C) (D)

3. The relative rate of catalytic hydrogenation of following alkenes is

(I) (II) (III) (IV)

(A) II > III > IV > I (B) I > IV > III > II
(C) III > IV > I > II (D) II > IV > I > III

Comprehension - II
Acid catalysed hydration of alkene give alcohol) In this reaction addition of water takes
place according to markownikov’s rule) Since intermediate carbocation is formed in this
reaction, rearrangement of carbocation takes place) In oxymercuration demercuration
reaction hydration of alkene takes place according to Markownikov’s rule) Oxymercuration
demercuration is a better process than the catalytic hydration of alkene because in
oxymercuration dermercuration no rearrangement is possible) In hydroboration oxidation
hydration of alkene takes place according to anti Markownikov’s addition) In HBO reaction
rearrangement is not possible) Both in Oxymercuration demercuation and hydroboration
oxidation intermediate carbocation are not formed)

4. 2-phenyl propene on acidic hydration gives :

(A) 2-phenyl-2-propanol (B) 2-phenyl-1-propanol
(C) 3-phenyl-1-propanol (D) 1-phenyl-2-propanol

5. The product formed in the following reaction is

CH3 i) BH3  THF

H3C 
ii) H O /OH
 Pr oduct
2 2

CH3

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OH
CH3
CH3
(A) H3C C (B) H3C
CH3
HO CH3

H3C OH H2 C CH2 CH CH3

(C) (D)
CH3 OH CH3

i) B H
6. CH3  C  C  H  2 6
ii) H O /OH
 A, A is
2 2

H3C CH3
(A) CH3—CH2—CHO (B)
O
(C) CH3—CHO (D) CH3—CH2—CH2—OH

MATRIX MATCH TYPE QUESTIONS

7. Match the Column

Column – I Column - II

CH3 CH3
CH2  
i) Hg(OAc )2 /H2 O
(A) ii) NaBH4 /OH (p)
H3C H3C OH

CH3 CH3

(B) CH2 

i) BH  THF
3
 (q) H3C
ii) H2O2 /OH
H3C OH CH3

CH3
CH3
CH3
(C) CH2 
H2O/H (r) H3C

H3C
OH

CH3
CH3
CH3
(D) CH2 
i) Hg(OAc )2 /CH3 OH
 (s) H3C
ii) NaBH4 /OH
H3C
OCH3

8. Match the Column

Column – I Column - II

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(A) n-Hexane 
 Benzene (p) Wurtz reaction

(B) Acetylene 
 Benzene (q) Frankland reaction

(C) CH3 – CH2 – Br 

 n-Butane (r) Aromatisation

(D) (CH3)3 C – X 
 (CH3)3C – C (CH3)3 (s) Polymerisation

9. Match the Column

Column – I Column - II
(A) CH3 – CH = CH2 
HCl
 (p) Nucleophilic addition

(B) CH3—CH = CH2 

NBS
 (q) Free radical addition
HBr
(C) CH3–CH = CH2 
peroxide
 (r) Electrophilic addition

(D) CH  CH 
HgSO4 /H2O
 (s) Free radical substitution

10. From the given sets, match appropriately

Set – I Set – II
H3C  H 2O 2  HBr
(A) CH2
(p) Free radical mechanism

(B) Cl  Cl 2  FeCl 3 (q) Elimination

(C) H3C CH  HCl (r) Electrophilic aromatic substitution

Br
(D)  NaNH 2 (s) Electrophilic addition
Br

11. Match each of the following compound in Column-I with the characteristic reaction in
column -II
Column-I Column- II

(A) H  C  C  H (p) Reduction with H 2 / Ni

(B) CH 3  CH  CH 2 (q) Hydroboration oxidation

(C) CH 3  C  C  CH 3 (r) Reaction with ammonical AgNO3

solution

(D) (s) Ozonolysis

(t) Reaction with NBS

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12. Match each of the compound in column I with the product of reductive ozonolysis in
Column-II

Column -I Column -II

(A) (p) formaldehyde

(B) CH 2  CH  CH  CH  CH 3 (q) Glyoxal

(C)  CH 3 2 C  CH  CH  CH 2 (r) Propane-1,3-dial

(D) CH 3  CH  CH 2 (s) Acetone

(t) Acetaldehyde
ASSERTION - REASONING TYPE QUESTIONS

13. STATEMENT – 1: Cis-2-butene gives meso compound with Baeyer’s reagent)

STATEMENT – 2: Baeyer’s reagent give anti addition reaction with alkenes)

14. STATEMENT – 1: Addition of Br2 to 1-butene gives two optical isomers)

STATEMENT – 2: The product contains one asymmetric carbon)

15. STATEMENT – 1: CH4 does not react with Cl2 in dark

STATEMENT – 2: Chlorination of CH4 takes place in sun light)

16. STATEMENT – 1: Acetylene reacts with sodamide to give acetylide

STATEMENT – 2: Acetylene is weaker acid than NH3

17. STATEMENT – 1: Reaction of cold alkaline KMnO4 and alkenes is regioselective

STATEMENT – 2: During the reaction of KMnO4 and alkene cyclic intermediates are formed)

18. STATEMENT – 1: Alkenes are more reative than alkynes for electrophilic addition reaction)
STATEMENT – 2: Alkyl carbocation is more stable than vinyl carbocation)

19. STATEMENT – 1: Cis-2-butene gives ( dl ) mixture with bromine

STATEMENT – 2: Bromine give anti addition with alkene

20. STATEMENT – 1: Carbon carbon double bond length in 2-butene is more than that 1-butene)
STATEMENT – 2: Hyperconjugation increases the bond length of carbon carbon double
bond)

21. STATEMENT – 1: Neopentane form one monosubstituted product)

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STATEMENT – 2: Neopentane is the isomer of n-pentane)

22. STATEMENT – 1: But-1-ene on reaction with HBr in presence of peroxide produces 1-

Bromobutane)
STATEMENT – 2: It involves the formation of primary carbocation)

EXERCISE – 4
SUBJECTIVE TYPE QUESTIONS

1. One mole of 1,2-Dibromopropane on treatment with x moles of NaNH 2 followed by treatment

with ethyl bromide gave 2- pentyne) The value of ' x ' is

2. The number types of monochloroalkanes formed by chlorination of isobutane is

3. The number of moles of CH 4 formed by reacting 96 grams of CH 3OH with excess CH 3 MgI
is

4. The number of chain isomers of alkane containing six carbon atom is

5. The number of different types of substitution products possible when bromine and ethane
react in presence of light is

6. The maximum nubmer of carbon atoms in the expected products of the following reaction

CH 3CH 2 Br + CH 3 - CH - CH 2 Br
CH 3 
Na / Ether
 Product

7. The number of possible enantiomeric pairs that can be product during monochlorination of
2-methylbutane is

CH 3


Cl2 , hv
M
8. (isomeric products)
H 3C  C5 H11Cl 
CH 3

The number of M is

9. Complete the following sequence of reaction with appropriate reagents

CH2


(1)
(X) 
(2)
(Y) 
(3)


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10. The hydrocarbon (A), adds one mole of H2 in the presence of platinum catalyst to form n-
hexane) When A is oxidized vigorously with KMnO4, a single carboxylic acid containing three
carbon atoms is isolated) Give the structure of (A) and explain)

11. Identify X, Y and Z in the following sequence of reactions giving stereochemical structures
wherever possible)

(i) CH3 CO3H

CH   (X)   (Y)  (Z)
(i) Na (i) H2
C (ii) —Br PdBaSO 4 (ii) H /H2O

12. An unknown compound C6H12(A) decolourises Br2 in CCl4 and is oxidized to a resolvable
carboxylic acid C4H9COOH by hot acidified KMnO4) Explain)

13. A hydrocarbon (A) of the formula C8H10, on ozonolysis gives compound (B) (C4H6O2) only)
The compound (B) can also be obtained from the alkyl bromide (C) (C3H5Br) upon treatment
with magnesium in dry ether followed by carbon dioxide and acidification) Identify (A), (B)
and (C) giving all the reactions involved)

14. An alkyl halide reacts with sodium in presence of dry ether to form 2, 5-dimethylhexane)
What is the structure of alkyl halide?

15. Chlorination of optically active 2-chlorobutane yields a mixture of isomers with the formula
C4H8Cl2)

a) How many different isomers would you expect to be produced? What are their
structures?

b) Which of these fractions would be optically active?

16. Find the reagents a, b, c & d for the following reactions

CH3H

a


H D

CH3H

b


D H
H3C H
CH3H

c


OH H


d
 CH3H

H OH

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17. Identify x, y, z and w in the following reaction:

H2SO4 /H2O BH3/THF

(W ) 
HBr
 z   (X) 
HBr
(Y)
H2O2/OH

18. An organic compound (A) C6H10 on reduction, first give (B) C6H12 and finally (C) C6H14 ) (A)
on reaction with ozone followed by hydrolysis in presence of Zn gives two aldehydes C 2H4O
(D) and C2H2O2 (E)) Oxidation of (B) with acidified KMnO4 gives acid (F) C3H6 O2 ) Determine
structures of (A) to (F) with proper reasoning)

19. An alkyl halide, (X), of formula C6H13 Cl on treatment with potassium tertiary but oxide gives
two.

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ANSWER KEY
EXERCISE-1
1. D 2. A 3. D 4. A 5. C
6. D 7. C 8. C 9. D 10. A
11. C 12. A 13. C 14. D 15. B
16. D 17. B 18. C 19. B 20. C
21. B 22. B 23. C 24. D 25. A

26. B 27. D 28. C 29. D 30. A

31. C 32. C 33. C 34. A 35. C
36. B 37. B 38. A 39. D 40. B
41. B 42. D 43. D 44. A 45. A
46. B 47. B 48. B 49. A 50. A

51. C 52. B 53. A 54. C 55. A

56. B 57. B 58. B 59. B

EXERCISE-2
1. B,C,D 2. B,D 3. A,B,C 4. C,D
5. B,C 6. A,B 7. A,B,C 8. A,B,D
9. B,C 10. A, C 11. B,C,D 12. A,C
13. C,D 14. A, B, D 15. A, B, C 16. A, B, C
17. A,B,C, D

EXERCISE-3
1. (B) 2 (A) 3. (A) 4. (A) 5. (B)

6. (A) 7. (A – r), (B – p), (C – q), (D – s)

8. (A – r), (B – s), (C – p,q), (D – q) 9. (A – r), (B – s), (C – q), (D – r)
10. (A – p), (B – r), (C – s), (D – q) 11. (A-p,q,r,s) (B-p,q,s,t) (C-p,q,s) (D-p,q,s,t)
12. (A-r) (B-p,q,t) (C-p,q,s) (D-p,t)
13. C 14. A 15. B 16. C
17. D 18. B 19. A 20. A
21. B 22. C
EXERCISE-4
1. 3 2. 2 3. 3 4. 5
5. 9 6. 8 7. 2 8. 6

O
H OH

9. 10. CH 3  CH 2  CH  CH  CH 2  CH 3 (A)

(X) (Y)

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11. C C HO OH
H H H H

(X) (Y) (Z)

CH3
C C COOH Br
12. 13.
CH3 – CH2 – CH – CH = CH2 (A) (B) (C)

CH3
14.
H3 C CH CH2 X

CH3 CH2Cl CH3 CH3 CH2 Cl CH3 CH3

CCl2 CHCl CHCl CHCl Cl H H Cl H Cl

; ;
   Cl H CH2
CH2 CH2 CHCl CH2 C2 H 5
15. (a) (b)
CH3 CH3 CH3 CH2Cl CH3 CH2Cl
4 possible isomers (I) (II) (III)

16. a)B2H6/CH3COOD b)B2D6/CH3COOH


c)H2O/H+ or Hg (OAc)2 / H2O/NaBH4 d)B2H6/H2O2/ OH

OH
17. (X) (Y) Br

(Z) OH (W) Br

A  CH  CH — CH3 (hexa  2,4  diene)

CH3 CH2CH = CH — CH2 — CH3
18. (B)
CH  CH — CH3

CH 3 CH 2 CH 2 CH 2 CH 2 CH 3 (C) CH 3 CHO (D)

CHOCHO (E) CH 3 CH 2 COOH (F)

CH3 CH3 H3C CH3 H3C CH3

H Cl C C CH C
19. CH3 CH3 H3C CH3 H3C CH2
(Y) (Z)
(X)

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