Chemistry

IUPAC Nomenclature +
Tautomerism

In One Shot Om Pandey, IIT Delhi

Topics
1 Catenation , Bonding , Hybridisation , Structural Formula

2 Degree of C , H , Alcohol , Amines

3 Degree of Unsaturation

4 Classifications of organic compounds

5 Naming of substituents

6 IUPAC Rule for Different Functional Groups

7 Tautomerism & Acidic Strength

The Catalyst
 Bonding in Organic compounds

Molecular Formula
 It indicates the linkage due to covalent bond
Structural Formula between different atoms in a molecule

Expanded Condensed Bond-line

QUESTION (27 Jan, 2024 / Shift-I)

Bond line formula of HOCH(CN)2 is :

H
CN
CN
A C B HO – CH
CN
HO CN

OH
CN D
C HO – CH CN CN
CN
Hybridisation of Carbon

Saturated Hydrocarbon Unsaturated Hydrocarbon

QUESTION (IIT-JEE 2003)

Which of the following represent the given mode of hybridization sp2 – sp2 – sp – sp
from left to right.

A H2C = CH – C  N B HC  C – C  CH

C H2C = C = C = CH2 D CH2

H2N
 PYQ

The state of hybridization of C2, C3, C5 and C6 of the hydrocarbon,

is in the following sequence :

A sp2, sp2, sp2 and sp

B sp, sp3, sp2 and sp3

C sp, sp2, sp2 and sp2

D sp, sp2, sp2 and sp2

Degree of Unsaturation
Find degree of unsaturation ?

CH CH2

Bicyclo Compounds Spiro Compounds

 𝑛𝐻 + 𝑛𝑥 − 𝑛𝑁
Formula for DU : DU = (𝑛𝑐 +1) −
2

C6H6O

C6H5Cl

C3H7N
 Number of carbon atoms attached to a carbon
Degree of Carbon
atom

Primary carbon

Secondary carbon

Tertiary carbon

Quaternary carbon

Super-primary
QUESTION (08 April, 2024 / Shift-I)

In the given compound, the number of 2° carbon atom/s is _____________

CH3 – C(CH3) – CH – C(CH3) – CH3

H H H

A Three

B One

C Two

D Four
 Degree of Hydrogen DOH is same as the DOC to which it is
attached.
CH3 — CH — CH3
CH3 — CH2 — CH3
CH3

Degree of Alcohol same as the DOC to which it is attached.

CH3 — CH2 — OH
OH
CH3 — C — CH3
CH3 — CH — CH3
CH3
OH
 Degree of Amines No of carbon attached to N

NH3

CH3 — CH2 — NH2

CH3 — N — H
CH3

CH3
CH3 — N — CH3 +
CH3 — N — CH3
CH3
CH3
QUESTION

Indicate the following as 1°, 2° and 3° amines.

A N–H B CH3
NH

C N D N – CH3
QUESTION

Indicate the following as 1°, 2° and 3° alcohol.

(A) OH (B) OH (C) OH

 Organic Compounds

Open chain compounds Cyclic Compounds

Aliphatic compounds
Acyclic compounds
Alicyclic Aromatic

Homocyclic Heterocyclic
Saturated Unsaturated
hydrocarbon hydrocarbon

Homocyclic Heterocyclic
JEE MAINS 2022 /28 July/Shift-I

Match List-I with List-II

List-I List-II
(A) (I) Spiro compound
O

(B) (II) Aromatic compound

(C) (III) Non-planar Heterocyclic compound

(D) (IV) Bicyclo compound

O
Choose the correct answer from the options given below

A (A)-(II), (B)-(I), (C)-(IV), (D)-(III) B (A)-(IV), (B)-(III). (C)-(I). (D)-(II)

C (A)-(III), (B)-(IV), (C)-(I), (D)-(II) D (A)-(IV), (B)-(III). (C)-(II). (D)-(I)

QUESTION (27 Jan, 2024 / Shift-I)

Cyclohexene is ___________ type of an organic compound.

A Benzenoid aromatic

B Benzenoid non-aromatic

C Acyclic

D Alicylic
IUPAC Nomenclature
Word Root : Number of carbon atoms Primary Suffix : It indicate the saturation
Present in the main chain Or unsaturation existing in the main chain.

No of Carbon Word Root

ane

ene

diene

yne

diyne

enyne
Secondary Suffix : It is used for the principal functional group .

Functional Group :
Group of atoms that is responsible for most of functions (behavior) of molecule.

Naming of Functional Groups

12 Functional Groups
Functional Groups Suffix Prefix

R — COOH Oic acid / Carboxylic acid Carboxy

R — SO3H Sulphonic acid Sulpho

O O
|| ||
—C—O − C − Anhydride / Carboxylic anhydride

O
||
—C—OR Alkanoate Alkoxy Carbonyl
Alkanoyl oxy
O
||
—C— X Oyl halide / Carbonyl halide Halo Carbonyl
Functional Groups Suffix Prefix

O
||
—C— NH2 amide (carboxamide) Carbamoyl

R—C N nitrile (carbonitrile) Cyano

O
||
—C— H al (carbaldehyde) Formyl / Oxo

O
||
—C— one Oxo
Functional Groups Suffix Prefix

— OH ol Hydroxy

— SH thiol Mercapto

— NH2 amine Amino

O
Senior & Junior Functional Group CH3 — C — CH2 — CH2 — NH2
JEE MAINS 2022 / 26 July/Shift-II

The correct decreasing order of priority of functional groups in naming an

organic compound as per IUPAC system of nomenclature is

A –COOH > –CONH2 > –COCl > –CHO

B –SO3H > COCl > –CONH2 > –CN

C –COOR > –COCl > –NH2. > –CHO

D –COOH > –COOR > –CONH2 > –COCl

AIEEE –
2003
Number of functional groups present in the following compound is :
NH2 O
H OH
NH
O O O O
O O
Primary Prefix : ‘ Cyclo ’ word is used for alicyclic compounds

Secondary Prefix : Normal substituent's and junior functional groups

–X

Alkane
Alkene

Alkyne

Benzene

CH2 —

– OR
Naming of Saturated Hydrocarbons
Rules for selection of main chain and numbering

Maximum number of carbon Lowest set of locants

More number of substituents Alphabetical order

Note - 2 same substituent : di
3 same substituent : tri
4 same substituent : tetra

Note - Comma b/w two counting

Hyphen b/w counting and words
 Cl Cl

Br

Cl

Cl
Cl
Complex Alkyl Group
QUESTION (08 April, 2024 / Shift-II)

IUPAC name of following hydrocarbon (X) is :

CH3 – CH – CH2 – CH2 – CH – CH – CH2 – CH3

CH3 (X) CH3 CH3

A 2-Ethyl-3,6-dimethylheptane

B 2-Ethyl-2,6-diethylheptane

C 2, 5, 6-Trimethyloctane

D 3, 4, 7-Trimethyloctane
Normal (n) : hydrocarbon which has straight chain
n – butane

n – pentane

n – hexane

Iso : Two methyl group at the end of linear chain

Isobutane

Isopentane Iso-octane

Isohexane
 Neo : Neopentane Neohexane

Sec. butyl

Tert. butyl Tert. pentyl

 QUESTION

The structure of isobutyl group in an organic compound is :

A CH3 – CH – CH2 – CH3

B CH3 – CH2 – CH2 – CH2 –

CH3
C CH3 C
CH3

CH3
D CH – CH2 –
CH3
Naming of Unsaturated Compounds

Maximum number of Number of sub. Lowest set of locants Alphabetical Order

Carbon with M. B.

CH3 —CH = CH2

CH3 —CH2 —CH = CH2

CH3 —CH = CH —CH —CH3

|
CH3
Maximum number of Number of sub. Lowest set of locants Alphabetical
CarbonNaming of Unsaturated Compounds
with M. B. Order

Cl
|
CH3 —C —CH2 —CH = CH2 C  CH
|
Cl

C  CH

HC  C —C  CH
JEE Mains 2018/ 18
April
The IUPAC name of the following compounds is :

A 3-ethyl-4-methylhex-4-ene

B 4, 4-diethyl-3-methylbut-2-ene

C 4-methyl-3-ethylhex-4-ene

D 4-ethyl-3-methylhex-2-ene
JEE Mains

The IUPAC name of the following compound is

CH3
H3C CH

CH3
CH2

A 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne

B 3, 5-dimethyl-4-propylhept-1-en-6-yne

C 3, 5-dimethyl-4-propylhept-6-en-yne

D 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
 Homologous Series
Alkane Alkene Alkyne Alcohol

A sequence of compounds with the same functional group , in which the members of the
series can differ by molecular formula of CH₂ and molecular mass of 14u .
Homologs have same general formula .
 QUESTION

The general molecular formula, which represents the homologous series of alkanols is

A CnH2nO

B CnH2n+1 O

C CnH2n+2 O

D CnH2n O2
AIEEE – 2005 The general formula CnH2nO2 could be for open chain

A Diketones

B Carboxylic acids

C Diols

D dialdehydes
 Functional Groups

7 Functional group 5 Functional group

O
|| – OH
—C — OH – SO3H

O O – SH
|| ||
—C —OR —C — NH2
– NH2
O O O
|| || ||
—C —O—C — R —C —Cl O
||
O —C —
||
—CN —C — H
7 Functional group 5 Functional group
Carbon present in functional Numbering is done from the side of
groups are always given the the chain which gives the lowest
position 1 . number to functional group

O
CH3 — C — OH CH3 — CH2 — CH — CH3
O OH
CH3 — CH2 — CH2 — CH2 — C —H

CH3 — CH2 — CH2

O
NH2
CH3 — CH2 — CH2 — C —NH2
 Selection of main chain / numbering

Functional group Multiple Bonds No. of carbon atoms No. of substituents

Lowest locant Alphabetical order

Note If first alphabet of the secondary suffix is a / e / i / o / u then e of primary

suffix will be dropped.

Lowest locant Functional group Multiple Bond Substituents

O
CH3 — C — CH2 — CH2 — OH
Naming of Cyclic Hydrocarbon

Functional group Multiple Bonds No. of carbon atoms No. of substituents

Lowest locant Alphabetical order

— OH

OH
All the factors are similar in cyclic and acyclic part then : Cyclic > Acyclic

Cl
CH2 — CH2 — CH3
CH — CH2 — CH3

Cl
QUESTION (27 Jan, 2024 / Shift-I)

IUPAC name of following compound (P) is :

(P)

A 1-Ethyl-5, 5-dimethylcyclohexane

B 3-Ethyl-1, 1-dimethylcyclohexane

C 1-Ethyl-3, 3-dimethylcyclohexane

D 1, 1-Dimethyl-3-ethylcyclohexane
QUESTION (JEE-Main 2017)

The IUPAC name of the following compound is :

A 1, 1-Dimethyl-2-ethylcyclohexane

B 2-Ethyl-1,1-dimethylcyclohexar

C 2, 2-Dimethyl-1-ethylcyclohexane

D 1-Ethyl-2,2-dimethylcyclohexar
 AIEEE – 2006
The IUPAC name of the compound shown below is
Cl

Br
A 2-Bromo-6-Chlorocyclohex-1-ene

B 6-Bromo-2-chlorocyclohexene

C 3-Bromo-1-chlorocyclohex-1-ene

D 1-Bromo-3-chlorocyclohexene
 Benzene as main chain

CH3 CH3 CH3

CH3
CH3
Toluene Xylene
CH3
CH3
CH3

Mesitylene
CH3 CH3 Cumene
Isopropylbenzene

CH = CH2
Styrene
Ethenylbenzene
 Br Br
m-Dibromo benzene p-Dibromo benzene

Br
Br

Cl Cl
NO2

CH3
NO2 Cl

CH2 – Cl Cl – CH – CH2 – CH2 – CH2 – CH3

Br

Benzyl chloride
1-(2-Bromophenyl)-1-chloropentane
 OH OH OH
CH3
o-Cresol m-Cresol p-Cresol
CH3
CH3

OH OH OH
OH
Quinol /
Catechol Resorcinol
Hydroquinone
OH
OH

OH
O2N NO2
Picric acid

NO2
JEE - Adv. 2017

The IUPAC name(s) of the following compound is (are)

H3C Cl

A 4-methylchlorobenzene

B 4-chlorotoluene

C 1-chloro-4-methylbenzene

D 1-methyl-4-chlorobenzene
QUESTION (31 Jan, 2024 / Shift-II)

Identify structure of 2, 3-dibromo-1-phenylpentane.

Br Br Br

A B
Br

Br Br

C D
Br Br
Alcohols Functional Group = Suffix Prefix

CH3 — OH

n-Propyl alcohol

Isopropyl alcohol
Glycerol
n-Butyl alcohol

Isobutyl alcohol

tert-Butyl alcohol
 OH

CH3
OH

Ph
OH
QUESTION (29 Jan, 2024 / Shift-II)
OH
According to IUPAC system, the compound is named as

A Cyclohex-1-en-2-ol

B 1-Hydroxyhex-2-ene

C Cyclohex-1-en-3-ol

D Cyclohex-2-en-1-ol
AIEEE – 2004

The IUPAC name of the compound is

HO

A 3, 3-dimethyl-1-hydroxycyclohexane

B 1, 1-dimethyl-3-hydroxycyclohexane

C 3, 3-dimethyl-1-cyclohexanol

D 1, 1-dimethyl-3-cyclohexanol
Amines Functional Group = Suffix Prefix

CH3 — CH2 — NH2

CH3
CH3 — CH2 — NH

CH3

N
CH3 CH3
 CH3 — CH — CH3 CH2 = CH — CH2 — NH2

NH2

OH
NH2

n-Propylamine Benzylamine

Isopropylamine
Allylamine Aniline NH2

o-Toluidine NH2
CH3

CH3
N
CH3
N,N-Dimethylaniline
 QUESTION (08 April, 2024 / Shift-I)

Given below are two statements :

Cl
Statement I : IUPAC name of compound A is 4-chloro-1, 3-dinitrobenzene .
O2N NO2
NH2
CH3
Statement II : IUPAC name of compound B is 4-ethyl-2-methylaniline.

C2H5
In the light of above statements, choose the most appropriate answer from the options given below :

A Both Statement-I and Statement-II are correct

B Statement-I is incorrect but Statement-II is correct
C Statement-I is correct but Statement-II is incorrect
D Both Statement-I and Statement-II are incorrect
Thiols Functional Group = Suffix Prefix

CH3 — SH

CH3 — CH — CH2
SH OH
Ketones Functional Group = Suffix Prefix

CH3 — C — CH3
O

CH3
O
QUESTION (31 Jan, 2024 / Shift-I)

Statement-I: IUPAC name of HO – CH2 – (CH2)3–CH2 – COCH3, is 7-hydroxyheptan-2-one.

Statement-II : 2-oxoheptan-7-ol is the correct IUPAC name for above compound.

A Statement-I is correct but Statement-II is incorrect.

B Both Statement-I and Statement-II are incorrect.

C Both Statement-I and Statement-II are correct.

D Statement-I is incorrect but Statement-II is correct.

Carboxylic Acid Functional Group = Suffix Prefix

O
||
H —C —OH

C —OH
CH3 — C — OH ||
O
O

O
||
C —OH
C —OH ||
O
C —OH
||
O
JEE MAINS 2023 / 8 April /Shift-II

The correct IUPAC nomenclature for the following compound is

O
CH2 CH3
H3C CH2 CH

COOH

A 5-Formyl-2-methylhexanoic acid

B 2-Methyl-5-oxohexanoic acid

C 2-Formyl-5-methylhexan-6-oic acid

D 5-Methyl-2-oxohexan-6-oic acid
QUESTION (29 Jan, 2024 / Shift-II)

The total number of ‘Sigma and Pi bonds in 2-formylhex-4-enoic acid is _______________.

 Common and IUPAC name of dicarboxylic acid

Oxalic acid Malonic acid Succinic acid Glutaric acid Adipic acid Piemelic acid

COOH COOH COOH COOH COOH COOH

COOH CH2 (CH2)2 (CH2)3 (CH2)4 (CH2)5

COOH COOH COOH COOH COOH

Aldehydes Functional Group =
Suffix Prefix

CH3 — CH = O

CH3 O
CH3 — CH2 — CH — CH2 — C — H
Br

CH3 — CH2 — CH CH — C — H
O
O
CH3 — CH2 — C — CH2 — C — H
O
JEE MAINS 2020/02 Sept/Shift-I

The IUPAC name for the following compound is :

CHO
CH3
H3C
COOH

A 2,5-Dimethyl-6-carboxy-hex-3-enal

B 6-Formyl-2-methyl-hex-3-enoic acid

C 2,5-Dimethyl-6-oxo-hex-3-enoic acid

D 2,5-Dimethyl-5-carboxy-hex-3-enal
QUESTION (30 Jan, 2024 / Shift-I)

Structure of 4-Methylpent-2-enal is

CH3 O O
A H2C = C – C – CH2 – C – H B CH3 – CH2 – C = CH – C – H
H H CH3

O O
C CH3 – CH2 – CH = C – C – H D CH3 – CH – CH = CH – C – H
CH3 CH3
Special Suffix

O
O
C —H
C — OH

O O
C — OH C —H
 O
Formaldehyde H–C–H

O
CHO
Acetaldehyde CH3 – C – H OH Salicylaldehyde

O
Acetone CH3 – C – CH3

O
COOH Salicylic acid
C – CH3 OH
Acetophenone

O
C
Benzophenone
Acid Anhydride
C — OH HO — C
O O

O O
CH3 — C — OH HO — C — CH3

C — OH HO — C — CH3
O O
O
||
C
O
C
||
O
Amides Functional Group = Suffix Prefix

O
||
H —C — NH2

O
||
C — NH2

O
||
CH3 —C — NH2
Nitrile Functional Group = Suffix Prefix

CH3 — C  N

CN
QUESTION (30 Jan, 2024 / Shift-II)

IUPAC name of following compound is

CH3 – CH – CH2 – CN
NH2

A 2-Aminopentanenitrile

B 2-Aminobutanenitrile

C 3-Aminobutanenitrile

D 3-Aminopropanenitrile
Phthal-
O O
C – OH Phthalic Acid C–H Phthalaldehyde

C – OH C–H
O O

O O
||
C – NH2 Phthalamide C Phthalic Anhydride
O
C – NH2 C
||
O O
Ester Functional Group = Suffix Prefix

Alkoxy Carbonyl

O Alkanoyl oxy
||
H—C —O—CH3

O
||
CH3 —C —O—CH2 —CH3
QUESTION

CH3 – C = CH – C – OCH3 is named in IUPAC as :

Cl O

A Methyl-3-chlorobut-2-enoate

B Methyl-4-chloro-2-pentanoate

C Methoxy-3-chloro butanol

D Methoxy-2-chloro butanone
Ester O O

( Main Chain )— C — O — R R — C — O — ( Main Chain )

O O
HOOC — CH2 — CH2 — C — O — CH3 CH3 — C — O — CH2 — CH2 —COOH
Acid Halide Functional Group =

O
||
CH3 — C —Cl

O
||
C —Cl

O
||
C —Cl
 Ether

R` — O — R
CH3 — O — CH3

O—
CH3 — O — CH2 — CH3

O — CH2 — CH3
 Tautomerism
H
|
—C — X = Y
|

Conditions (i) Acidic / Basic medium

(ii) sp3 carbon with at least 1 hydrogen attached to –M group
It involves change in the position of  Bond and hydrogen atom.
Enolisable Hydrogen
O
O
||
||
CH3 —CH = CH —C —CH3
CH3 —C —CH3

O
H H

O O

H H
% Enol Content

H H

Stability of Enol
(1) Aromaticity (3) Hydrogen Bonding

(2) Hyper-Conjugation (4) Resonance

% Enol Content Hydrogen Bonding

1, 3 diketone

1, 2 diketone

O O

O
O
% Enol Content

O
H O O CH3 ||
| || || —C — H
CH2 —C — H CH3 —CH —C — H
| H2C
H |
H
QUESTION (27 Jan, 2024 / Shift-I)

Highest enol content will be shown by :

O
O O
A B
O O

O
O
C D O O

O
 Benzoic Acids
O O O
|| || ||
C —OH C —OH
C —OH

CH3 NO2
Ortho Effect Applied for ortho substituted Benzoic Acid

O O O O
|| || || ||
C —OH C —OH C —OH C —OH
G

G
G
If all B.A.’s are ortho – substituted then Ka is decided by SIR effect.
O O O O
|| || || ||
C —OH C —OH C —OH C —OH
CH3 C2H5

O O O
|| || ||
C —OH C —OH C —OH
HO OH OH

OH
JEE Adv. 2019

The correct order of acid strength of the following carboxylic acids is

O O
H O
MeO OH
H OH
OH OH H3C
(I) H (II) (III) O
(IV)
A (I) > (III) > (II) > (IV)

B (III) > (II) > (I) > (IV)

C (II) > (I) > (IV) > (III)

D (I) > (II) > (III) > (IV)

2023/24 Jan/Shift-II

Which will undergo deprotonation most readily in basic medium?

O O O O O O

MeO OMe OMe

A B C

A A only

B C only

C Both A and C

D B only
No of Resonating Structures

O-

O-
 Chemistry

GOC
In One Shot Om Pandey, IIT Delhi
 Organic Chemistry

ISOMERISM

In One Shot Om Pandey, IIT Delhi

Topics
1 Isomer

2 Types of isomerism

3 Structural Isomerism & No of isomers

4 Stereoisomerism & No of isomers

5 Confirmational Isomerism
12 BOARD
TH
Degree of carbon

Degree of unsaturation

Isomers Compounds with same molecular formula but different

physical and chemical property.
 Isomers

Structural isomers Stereoisomers

Different arrangement of atoms or Different arrangement of atoms or

groups within the molecule groups in 3D space
1) Chain isomers 1) Configurational isomers
2) Position isomers a) Geometrical isomers
3) Functional isomers b) Conformational isomers
4) Metamers
2) Conformational isomers
5) Tautomers
Structural Isomers
Skeletal isomers , Linkage isomers & Constitutional isomers
Compounds having same molecular formula but different structure
 Chain Isomers
Isomers having different size of main carbon chain / side alkyl chain
Same nature of F.G. , M.B. , Substituents

C4H10 C5H12 3 isomers

C6H14
5 isomers
QUESTION (04 April, 2024 / Shift-I)

The number of different chain isomers for C7H16 is ______________.

Positional Isomers Compounds having same MF but different
position of FG / MB / Substituents

OH

OH

Cl Cl

Cl
IIT-JEE 2014

The correct combination of name for isomeric alcohols with molecular formula
C4H10O is/are

A tert-butanol and 2-methylpropane-2-ol

B tert-butanol and 1, 1-dimethylethan-1-ol

C n-butanol and butan-1-ol

D isobutyl alcohol and 2-methylpropane-1-ol

Find no of isomers with MF C8H10 ?

 Functional Isomers Compounds having same molecular formula but
different functional group .

Acid & Ester 1°, 2°, 3° Amines

Alcohol & Ether

Ketone & Aldehyde

1°, 2°, 3° Amides

Alkene & Alkyne

Enol and Alcohol

Ring – Chain Isomerism

Cyclic Alkane & Alkene

Cyclic Alkene & Alkyne

 Compounds having same nature of functional groups but different
Metamers
nature of alkyl groups along polyvalent functional group

Ether 2o Amide

Thio-Ether 3o Amide

2o Amine Ester

3o Amine Ketone
QUESTION (05 April, 2024 / Shift-II)

Match List-I with List-II

List-I List-II
(A) 1-propanol and isopropanol (I) Metamerism
(B) Methoxypropane and ethoxyethane (II) Chain Isomerism
(C) Propanone and propanal (III) Position isomerism
(D) Neopentane and Isopentane (IV) Functional Isomerism

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

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

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

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

JEE Mains-2021

Which one of the following pairs of isomers is an example of metamerism?

CH3

A CH3CH2CH2CH2CH3 , H3C – C – CH3

O CH3

B C6H5 , H5C6 H
O
OH
OH
C H5C6 ,
H5C6
O O
D ,
 No of Structural Isomers
No of carbon DU = 0 DU = 1 ( Cyclic )

C3

C4

C5
How many structural isomers are possible for following MF ?
C4H9Cl Different type of carbon
with atleast 1 H

C4H9OH Alcohol C4H10O Ether

How many structural isomers are possible in cyclic form for following MF ?
C4H7Cl

C4H8O Cyclic Alcohol C4H8O Cyclic Ether

Ketones & Aldehydes

C4H8O

C5H8O
Cyclic Ketones
JEE Mains - 2021

Compound with molecular formula C3H6O can show :

A Positional isomerism

B Both positional isomerism and metamerism.

C Metamerism.

D Functional group isomerism.

 Wedge Dash Projection
F
Wedge : Towards Observer H
Dash : Away from observer Br
HO

Fischer Projection
OH

F Br
Vertical line : Away from observer
H
Horizontal line : Towards observer
 Stereoisomerism Same structural formula but different orientation
in space

CH3 CH3 CH3 H

C C C C
H H H CH3

Restricted Rotation :
 Geometrical Isomerism

Conditions Restricted Rotation

Two different groups at each restricted point
The groups / atoms showing G.I. must be in same plane. ( 1  2 )

1. In Double bond system 2. In Ring system

D D D Cl
C C C N
H H H H Cl

N N
H H
Which will show Geometrical Isomerism ?

H H F
(1) C C
H H (4)
Cl

D D
(2) H C C
H

I F
(3) C C
Br Cl
JEE Mains 2020 / 5 Sept/Shift-II

Among the following compounds, geometrical isomerism is exhibited by :

CHCl CHCl

A B
CH3

CH2 CHCl

C D
H3C CH3
Cl
 Cis – Trans Nomenclature

a a a b
C C C C
b b a b

D D
C C
H H

Cl F
C C
F Cl
 Syn — Anti Nomenclature

R R R
C N C N C N
H G H OH H NH2

R G
C N
H

R
N N N N
R R R
Note : If n is the no. of carbon atoms present in a ring then
(i) n < 8 (ii) n  8
JEE Mains 2020 / 6 Sept / Shift-I

Which of the following compounds shows geometrical isomerism ?

A pent-2-ene

B 4-methylpent-1-ene

C 4-methylpent-1-ene

D 2-methylpent-1-ene
E / Z Nomenclature a b a d
C C C C
c d c b
 CIP Rule [ Sequence Rule ]
1) Group having first atom with higher atomic no. is senior . Cl Br
C C
F I

2) The higher mass isotope is senior. Cl D

C C
F H

3) If first atom of group is identical then second atom is observed for seniority.

Cl CH2 — CH3 CH3 CH2 — OH

C C C C
F CH2 — H I CH2 — NH2
4) Group having D.B. / T.B. are treated as following.

F
C C
Cl
JEE(Main) 2017 Online

In the following structure, the double bonds are marked as I, II, III and IV
II

III

I IV

Geometrical isomerism is not possible at site (s) :

A I

B III

C I and III

D I and IV
 JEE(Main) 2015

Which of the following compound will exhibit geometrical isomerism?

A 1-Phenyl-2-butene

B 3-Phenyl-1-butene

C 2-Phenyl-1-butene

D 1, 1-Diphenyl-1-propene
 Physical Properties of G.I.

Dipole moment Stability

Boiling point Melting point

Solubility in water

Br H Br Br
C C C C
H Br H H
AIEEE 2002 ( H.W. )

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
Polarimeter Experiment
+15°0 –15°
+30° –30°
+45° –45°

 → 0o
Optically Inactive

Polarizer Plane Sample cell Analyzer

Polarised Light
 → (+) , Clockwise
Dextro-rotatory
compound
Optical Rotation :

 → (-) , Anti-clockwise
Leavo-rotatory
compound
 Specific Rotation [  ]

l → dm
C → gm/ml
 → degree

Specific Rotation is the degree of rotation observed if a 1 dm tube is used and compound
has concn 1gm / ml.
Chiral Centre / Chiral Atom / Asymmetric Atom
1. sp3 Hybridisation
2. 4 different groups/atoms

How many chiral atoms are present in following compounds ?

H
H
Cl
+ N
(a) (b) N CH3
(c)
C2H5 O N
Br
O H
H5C2 D
(d) Si (e) CH3 S C2H5
H3C H
JEE Mains 2022 /29 June/Shift-I

Observe structure of the following compounds

Cl NH2
OH OH
H2N
O O

OH

The total number of structures compounds which possess asymmetric atoms

is ______________.
Chiral Compounds A compound which is non-superimposable on its mirror image
Asymmetric compounds F
H

HO Br

OH

F Br

A compound having only one chiral carbon is Chiral / Optically Active.

 AIEEE 2004

Amongst the following compounds, the optically active alkane having lowest molecular
mass is

A CH3 – CH2 – CH2 – CH3 B CH3 – CH2 – CH2 – CH3

C CH3 – C D CH3 – CH2 – C  CH

C2H5
AIEEE 2004

Among the following four structures I to IV.

CH3 O CH3 H CH3

C2H5 – CH – C3H7 CH3 – C – CH – C2H5 H – C C2H5 – CH – C2H5

(I) (II) (IV)
H
(III)
It is true that :

A All four are chiral compounds

B Only I and II are chiral compounds

C Only III is a chiral compound

D Only II and IV are chiral compounds

 Rule for Correct Fischer Projection
On the vertical line , main chain is taken with first carbon at top.

CH2OH CH CHO
OH

CH3 CH COOH
NH2
 Nomenclature

Absolute Configuration
Relative Configuration
R – S Nomenclature
D – L Nomenclature

Standard : Glyceraldehyde

CHO CHO
H OH HO H
CH3 CH3

Note : Applied only in Correct Fischer Projection

 R - S Nomenclature - Fischer Projection
Apply CIP Rule and find priority order . a
c b

Cl CHO
I Br HO CH3
F H
If lowest priority group is at horizontal line then
O
a
CHO C H
c d H Cl HO H
b H3C
H OH

CH2OH

Odd & Even Exchange

CHO
H Cl
H3C
JEE (Main) 2016
CO2H
H OH
The absolute configuration of is
H Cl

CH3

A (2S, 3R)

B (2S, 3S)

C (2R, 3R)

D (2R, 3S)
R - S Nomenclature in Wedge Dash Projection

CH3
H
F
Cl

C2H5 C2H5
OH H
H2N H H2N
OH
 Wedge – Dash Projection Fischer Projection

D
H

F
I

D
I
F
H

D
F

H
I
 Find D – L Nomenclature for following ?

CH3
HO H
CHO

COOH
H
H2N CH3
 AIEEE 2008

HO2C CO2H
The absolute configuration of is
H
H OH
OH
A R, R

B R, S

C S, R

D S, S
 Elements of Symmetry

Plane of Symmetry Centre of Symmetry

Imaginary plane which bisects the molecule in COS is a point from which two same
two equal halves, in such a way that each half atom/groups are at same distance.
of the molecule is a mirror image of other half.

H CH3 CH3 HO H
CH3 CH3 HO

H H H OH
H H H OH
 Plane of symmetry & Centre of symmetry

H D
Optically Active
F C Cl C
Acyclic Compounds POS
H H
Cl F
Cyclic Compounds POS
COS

CH3 CH3
CH3 CH3
H OH HO H
H OH H OH
CH3 H D
CH3
 AIEEE 2007

Which of the following molecules is expected to rotate the plane of polarized light?
NH2
H2N COOH CHO
H
(1) H (2) H2N H (3) HO H (4)
Ph Ph H CH2OH
SH
 IIT-JEE-2008

The correct statement(s) about the compound given below is (are).

H
Cl
CH3
H3C
Cl H

A The compound is optically active

B The compound possesses centre of symmetry

C The compound possesses plane of symmetry

D The compound possesses axis of symmetry

Enantiomers Br Br
1 or 2 chiral carbon Cl I l CI

Mirror Images F F

Non-superimposable

Diastereomers CH3 CH3

HO H H OH
2 chiral carbon
H OH H OH
Neither mirror images CD3 CD3
Nor-superimposable
 Physical Properties of Enantiomer & Diastereomer

CH3 CH3 CH3 CH3

HO H H OH D I D I
H OH HO H Br Cl Cl Br
CH3 CH3 F F

CH3 CH3 CH3 H

C C C C
H H H CH3

Enantiomers have similar physical properties except the opposite sign of specific rotation .
Diastereomers have different physical properties ( melting points, boiling points,
densities, solubilities, refractive indices, dielectric constants and specific rotations ).
JEE Mains 2022 / 29 July/Shift-II
CH3
Statement I : The compound NO2
is optically active. (A)
H

CH3 CH3
O2N
Statement II : The compound is mirror image of above compound A . H CH3

A Both statement-I and Statement-II are correct

B Both statement-I and Statement-II are incorrect

C Statement-I is correct but Statement-II is incorrect

D Statement-I is incorrect but statement-II is correct

 Meso Compound
Min. 2 chiral carbon Opposite configuration Same connectivity

CH3
H C2H5
H C2H5
CH3

Properties of Meso compound

(i) Meso compounds are optically inactive due to internal compensation of rotation of PPL.

(ii) Meso compound and its mirror image are identical.

AIEEE 2004

Which of the following will have a meso-isomer also ?

A 2-Chlorobutane

B 2, 3-Dichlorobutane

C 2, 3-Dichloropentane

D 2-Hydroxypropanoic acid
 Racemic Mixture
Equi-molar mixture of enantiomers

Br Br
Cl I l CI
F F

Note :
Racemic mixture is optically inactive due to external compensation of rotation of PPL .
 Asymmetric Nitrogen : Amine Inversion
Two enantiomers of amines always exist as racemic mixture hence optically inactive.

H
Cl Me

N N — Me
Me
C2H 5 CH3

Nitrogen salts and cyclic amines will not undergo amine inversion.
Geometrical & Optical Isomerism Allenes / Spirans / Cycloalkylidenes

Cl H
Br F H H
C C C C H Cl
I D D D

Cl l

F Br
JEE Mains 2023/01 Feb/Shift-I

The total number of chiral compound/s from the following is _____________.

Ph

OH
O O Cl
COOH

CH2 OH
COOH
HO OH
OH
OH
HO2C COOH
HO OH
COOH
OH
Biphenyls

O2N F I I I I

I Cl
I l

CI Br

F Br
IIT - JEE 2007

Statement-1 : Molecules that are not superimposable on their mirror images are chiral.
Statement-2 : All chiral molecules have chiral centres .

A Statement-1 is true, statement-2 is true; statement-2 is a correct explanation for

statement-1.

B Statement-1 is true, statement-2 is true; statement-2 is NOT a correct explanation

for statement-1.

C Statement-1 is true, statement-2 is false.

D Statement-1 is false, statement-2 is true.

No of stereoisomers
1 Stereo centre : D – CH – CH2 – CH3 CH3 – CH = CH – CH3

CH3

2 Stereo centre :

CH3 – CH – CH – CH3 CH3 – CH – CH – C2H5 CH3 – CH = CH – CH – OH

OH OH OH OH CH3
2 Stereo centre :
CH3 – CH = CH – CH = CH –CH3 CH3 – CH = CH – CH = CH –C2H5

3 Stereo centre :

H3C(HO)HC – CH = CH – CH(OH)CH3 H5C2(HO)HC – CH = CH – CH(OH)CH3

AIEEE 2009

The number of stereoisomers possible for a compound of the molecular formula

CH3 – CH = CH – CH(OH) – Me is :

A 2

B 4

C 6

D 3
 IIT-JEE 2009

The correct statement(s) about the compound H3C(HO)HC – CH = CH – CH(OH)CH3 (X)

is (are):

A The total number of stereoisomers possible for X is 6.

B The total number of diastereomers possible for X is 3.

C If the stereochemistry about the double bond in X is trans, the number of

enantiomers possible for X is 4.

D If the stereochemistry about the double bond in X is cis, the number of

enantiomers possible for X is 2.
JEE (Advanced) - 2018

For the given compound X, the total number of optically active stereoisomers is …………

HO HO
This type of bond indicates that the configuration at the
specific carbon and the geometry of the double bond is fixed
This type of bond indicates that the configuration at the
HO HO specific carbon and the geometry of the double bond is NOT
X fixed
 Conformational isomerism
Free rotation

Sawhorse Projection Newman Projection

Conformations :
Different arrangements of atoms that can be converted into one another by rotation
about single bonds are called conformations .
 Dihedral Angle
The angle between C – X and C – Y in X – CH2 – CH2 – Y

X
X Y
Y

Staggered conformation
Eclipsed conformation

Skew conformation : Other than Staggered & Eclipsed

 Factors affecting stability of conformations

Torsional Strain : Any deviation from the X

staggered conformation X
Y Y
Pitzer strain or Eclipsing strain

Vander Waals Strain : It is due to steric-crowding .

 Conformational Analysis of Ethane

Energy Profile of Ethane

POTENTIAL ENERGY

12.5
kJ/mol

0° 60° 120° 180° 240° 300° 360°

DIHEDRAL ANGLE
JEE Mains-2022

Staggered and eclipsed conformers of ethane are :

A Polymers

B Rotamers

C Enantiomers

D Mirror images
Conformational Analysis of Butane
 Conformational Analysis of Butane

POTENTIAL ENERGY

19 kJ
16 kJ
/mol
/mol
3.8 kJ/mol

0° 60° 120° 180° 240° 300° 360°

DIHEDRAL ANGLE

n-Butane exists as 3 conformers one anti and two gauche .

JEE Mains-2022

Arrange the following conformational isomers of n-butane in order of their increasing

potential energy
CH3 CH3 CH3 HH
H CH3 H
H CH3
I II III IV
H H H H
H H H H H H HC CH
3 3
CH3 H

A II < IV < III < I

B I < III < IV < II

C II < III < IV < I

D I < IV < III < II

 IIT – JEE 2010

In the Newman projection for 2, 2-Dimethylbutane

X
H3C CH3

H H

Y
X and Y can respectively be:

A H&H

B H & C2H5

C C2H5 & H

D CH3 & CH3

 IIT-JEE 2004

Newman projection of Butane is given, C-2 is rotated by 120° along C-2 & C-3 bond in
anticlockwise direction the conformation formed is :
CH
4 3
H H
3 2
H H
1
CH3
A Anti

B Fully eclipsed

C Gauche

D Partially eclipsed
Conformational Enantiomers CH3 CH3
H CH3 CH3 H
The gauche conformers of butane
are mirror images of each other. H H H H
H H

Conformational Diastereomers CH3 CH3

H CH3 H
Gauche conformations and anti conformation H
of butane are not mirror images of each other.
H H H H
H CH3
 Case of Intramolecular Hydrogen Bonding

G – CH2 – CH2 – OH where G = – OH , – NH2 , – F , – NR2 , – NO2 , – COOH ,–CHO

2-Flouroethanol

Gauche form is more stable than the anti-form due to intra molecular hydrogen bonding.
AIEEE 2006

Increasing order of stability among the three main conformations (i.e. eclipse, anti,
gauche) of 2-fluoroethanol is

A eclipse, gauche, anti

B gauche, eclipse, anti

C eclipse, anti, gauche

D anti, gauche, esclipse

AIEEE / JEE AD

Which of the following conformers for ethylene glycol is most stable :

OH OH
OH H

A B
H H HO H
H H H H

OH OH
H OH H H

C D

H H H H
H OH
IIT-JEE 2012 Which of the given statement(s) about N, O, P and Q with
respect to M is (are) correct ?

Cl CH3 CH3
HO H HO H
H H OH HO H
OH
HO Cl H CH3 HO
H OH H
HO H HO H
CH3 Cl CH3
Cl Cl
A M and N are non-mirror image stereoisomers.

B M and O are identical

C M and P are enantiomers

D M and Q are identical

JEE ( Advanced ) - 2014

The total number(s) of stable conformers with non-zero dipole moment for the
following compound is (are) :

Cl
Br CH3
Br Cl

CH3
JEE Adv. 2019
Total number of isomers considering both structural and stereoisomers, of cyclic
ethers with the molecular formula C4H8O is ____________
O
O O O
O
(S)
CH3 * CH3 CH3 (R)
CH3
(1 isomer)
(1 isomer) (2 isomers)

O O O O
CH3 * (S) (R)
CH3 CH3 CH3
CH3
(1 isomer) (2 isomers)

O O O O
(R) (R) (S)
(S) (R) (S)
H3C * * CH3 H3C CH3 H3C CH3 H3C CH3
(3 isomers)
JEE Mains 2022 / 27 June / Shift-I

Total number of possible stereoisomers of dimethyl cyclopentane is ________________.

CH3 CH3 CH3

R R S
CH3 CH3 CH3
S R S

CH3 CH3 CH3

R R S

S R S
CH3 CH3 CH3

Out of six isomers, two are meso compounds and are optically inactive
Therefore, only 4 isomers will be optically active.
QUESTION (30 Jan, 2024 / Shift-II)

Number of geometrical isomers possible for the given structure is/ are _______________.
D
H H

D
 Organic Chemistry

HYDROCARBON

In One Shot Om Pandey, IIT Delhi

Topics
1 Solvent , Electrophile , Nucleophile

Formation of Carbocation , Carbanion ,

2
Radicals ( Reactions with Metals )

3 Acid Base Reaction

4 Reactions of Alkane , Alkene , Alkyne & Benzene

5 Stereo-chemistry of Reactions of Alkene

6 Physical Properties
Non-polar Solvent Solvent Polar Solvent

Carbon Tetrachloride Water

Ethyl Alcohol
Benzene

Acetone
Cyclohexane
Tetrahydrofuran
 Solvents Polar Protic Aprotic
CH3 CH3
S
O
Dimethyl sulphoxide

CH3
H—C—N
O CH3
Dimethyl formamide

CH3
CH3 — C — N
O CH3
Dimethyl acetamide
Electrophile

Electron deficient species. BH3

Having vacant orbital with incomplete octet . BF3

Species having complete or partial ve charge on central atom. AlCl3

   ZnCl2
NO2 N=O X R–C=O
FeCl3

O O O O Cl
O C O
S C P R C Cl C
O O R R Cl Cl Cl Cl
Cl Cl
Nucleophile
ve charge loving species

Charged : R– H– Cl– Br– SH– OH– R — O–

Neutral : H — O R—O NH3 R — NH2

H
H

R— CH CH — R R—C C—R
Formation of Carbocation BF3 / BCl3 / AlCl3 / SbCl5

HI / HCl / H2SO4 / HNO3

Cl + SbCl5

CH3
|
CH3 —C —Cl + AlCl3
|
CH3

O
||
R —C —Cl + AlCl3
 |
H+
—C — O
|
H

CH AgNO3 (aq.)

Br
 Acid - base reaction

NaOH

NaOEt

NaH

NaNH2

Na

NaHCO3
 Formation of Carbanion

NaH

H H

H
| NaNH2
O2N —CH —CH2
|
F

Na
R—C C—H
20 July, 2021 (Shift-II)

Metallic sodium does not react normally with :

A Gaseous ammonia

B Tert-butyl alcohol

C But-2-ene

D Ethyne
 Reactions With Metal

Mg
CH3 — Br
ether

Li
CH3 — Br
ether

Zn
CH3 — Br

Zn
CH3 — Br
HCl
27 Aug, 2021 (Shift-I)

Cl
dry ethanol
+ Mg [A] P
ether

CH2CH3 O – CH2CH3
A B

C D
 M + R–X

Na
Wurtz Reaction : CH3 – Br
Dry ether

Cl
Na
Fitting Reaction : ether

Cl
Wurtz-Fitting Reaction : CH3 – Cl + Na
ether

Frankland Reaction : Zn
I 

I
Ullmann Reaction : Cu

Preparation of Alkane
Na
Wurtz reaction R — Cl Dry ether

Cl Cl

Cl Cl

Cl

Cl
 Na
Br – CH2 – CH2 – CH2 – Br
ether

Cl
Zn
H – Cl

Zn/Cu couple
CH3 – I Ethanol

OH
Br Na
Elimination Reaction

Addition Reaction
Alkene

Electrophilic Addition Reaction

Reactivity of an Alkene :
 CH2 CH2
Type - iii H + / D+

Cl+ / NO+

Hg2+ / Hg+ X
Hydrohalogenation of Alkene Markovnikov’s Rule : Electrophile
adds to the less substituted carbon

CH3 — CH CH2
HI

EDG — CH CH2
HI

EWG — CH CH2
HI
08 April, 2019 (Shift-II)

Which one of the following alkenes when treated with HCl yields majorly an anti
Markovnikov product ?

A F3C – CH = CH2

B Cl – CH = CH2

C CH3O – CH = CH2

D H2N – CH = CH2
06 Sept, 2020 (Shift-I) The major product of the following reaction is :

CH3

2HBr

NO2

CH3 CH3
H3C Br Br CH3
Br Br
A B C D
Br Br
Br Br
NO2 NO2 NO2 NO2
Rearrangement

HBr
Hydrogenation of Alkene

H2
CH3 — CH CH2
Pt
JEE ( Advanced ) - 2015

Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is (are)

H Br
H Br
A B H2C CH3
H3C CH3

H Br
H2C Br H
C D H2C CH3
CH3
Halogenation of Alkene

Br2
CH3 — CH CH2 CCl4

Br2
Ph — CH CH2 H2O
 NOCl
Ph — CH CH2

ICl
CH3 — CH CH2
09 Jan, 2019 (Shift-I) The major product of the following reaction is

Br2
EtOH

OEt OEt
Br
A B

Br OEt
OEt OEt
C D
13 April, 2023 (shift-II) Major product ‘P’ formed in the following reaction is :

OH
Br2
NaHCO3
P
O

Br
Br OH Br O
A B O
O
Br
C Br OH D OH

O O
Hydration of Alkene

Acid Catalysed Hydration

Oxymercuration – Demercuration

Hydroboration – Oxidation

Acid Catalysed Hydration

CH3 — CH CH2 H+ / H O
2
Acid Catalysed Hydration

CH3
H3C
Dil. H2SO4
H
 Oxymercuration – Demercuration

Hg(OAc)2
CH3 CH CH2
H2O

(i) Addition of water by Markovnikov’s Rule

(ii) Formation of cyclo-merquric ion [ Non – classical carbocation ]
(iii) Rearrangement is not possible.
(iv) Attack of H2O as nucleophilic on more substituted partial carbocation.
 Hydroboration – Oxidation
BH3
CH3 CH CH2 THF

(i) Syn-Addition of water by Anti-Markovnikov’s Rule

(ii) Formation of 4 membered transition state
Syn-Dihydroxylation by Baeyer’s Reagent

CH3 CH CH2

R—C C—R
Syn-Dihydroxylation by OsO4

CH3 CH CH2
 Anti-Dihydroxylation by Per Acid

Per-acetic acid Trifluoro peracetic acid Hydrogen Peroxide

RCO3H
CH3 CH CH2
 Stereo-chemistry in Reactions of Alkene

Anti-addition Syn - addition

Br2 / CCl4 H2 / Pd

Br2 / H2O BH3 / THF

H2O2 / OH-
HOBr
Cold and Dil. KMnO4
Hg(OAc)2 / H2O
NaBH4
OsO4

RCO3H
H3O+
Hg(OAc)2 / H2O BH3 THF
NaBH4 H2O2 OH–

D D

RCO3H KMnO4
H3O+ 0°C , OH–

D D

HOCl H2
Pt

D D
Ph H
C Cold dil
NaOH / KMnO4
C
H Ph

Ph H
C Cold dil
Alkaline KMnO4
C
Ph H
 H H
RCO3H
C C
H3O+
CH3 CH3

H CH3
RCO3H
C C
H3O+
CH3 H
 H H
Cl2 Br2
C C
CCl4 H2O
CH3 CH3

H CH3
Cl2 Br2
CCl4
C C H2O
CH3 H
 Kharasch Effect or Peroxide Effect Reagents : HBr / R2O2 , hv

R2O2/hv
R — CH CH2 + HBr

Mechanism :

hv
R—O—O—R

R — O• + H — Br

R — CH CH2 + Br•

•
R — CH — CH2 — Br + H — Br
H2O2 H2O2
HCl
Ph— CH CH2 HBr
 Electrophilic addition reaction of Alkynes
ENu
R— C C —H

Br2
R—C C—H CCl4

Br2
R—C C—H H2O

HBr
R—C C—H

HOBr
R—C C—H

KMnO4
R—C C—H
OH-
Test for Unsaturation

Br2 Br2
R—C C—R H2O R — CH CH — R H2O

Red Brown colour of the solution of bromine water is decolourised due to unsaturation.

Br2 Br2
R—C C—R CCl4 R — CH CH — R CCl4

Reddish orange colour of the solution of bromine in carbon tetrachloride is decolourised.

KMnO4 KMnO4
R—C C—R R — CH CH — R OH-
OH-

Colour changes from Pink purple (Bayer’s reagent) to Brown .

Hydrogenation
H2 / Pd
R—C C—R

H2 / Pd / BaSO4
Lindlar’s Catalyst

R—C C—R

Na / Liq. NH3

Na
R—C C—H
Liq. NH3
16 March, 2021 (Shift-I)

Which of the following is Lindlar catalyst?

A Partially deactivated palladised charcoal

B Cold dilute solution of KMnO4

C Zinc chloride and HCl

D Sodium and Liquid NH3

JEE Adv. 2021

The major product formed in the following reaction is :

NaNH2
Na
liq. NH2

A B

C D
 D2 / Pd Br2 / CCl4
CH3 — C C — CH3
CaCO3

Na Br2 / CCl4
CH3 — C C — CH3
Liq. NH3
01 Feb, 2023 (Corrected) But-2-yne is reacted separately with one mole of
Hydrogen as shown below :
Na Pd/C
B liq. NH3
CH3 – C  C – CH3  A

Identify the incorrect statements from the options given below:

(A) A is more soluble than B.
(B) The boiling point & melting point of A are higher and lower than B respectively.
(C) A is more polar than B because dipole moment of A is zero.

A (B) , (C) B (B), (C)

C (C) only D (A) and (B)

 Addition of H2O

HgSO4 , H2SO4
Me — C C—H
H2O

BH3
Me — C C—H
THF
24 Feb, 2021 (Shift-I)

Which one of the following carbonyl compound cannot be prepared by addition of

water on an alkyne in the presence of HgSO4 and H2SO4?

O O
A CH3 – CH2 – C – H B CH3 – C – CH2CH3

O O
C
D C – CH3 D CH3 – C – CH3
06 Sept, 2020 (Shift-I)

The major product obtained from the following reaction is :

Hg2+/H+
O2N CC OCH3 H2O

OCH3 OH
O

A B
O
O2 N O 2N
OCH3
OH O

D
C
O O 2N
O2N
 Ozonolysis
Reductive Ozonolysis Oxidative Ozonolysis
i. O3 i. O3

ii. Zn/H2O ii. H2O2

DMS

CH3 CH CH2
 Reductive Ozonolysis Oxidative Ozonolysis

CH3 CH CH2

CH3 CH CH CH3

CH3 — C C — CH3

NOTE : KMnO4 / H+ or alkaline KMnO4 with Heat gives same product as in Oxidative
Ozonolysis with alkene and alkyne
12 April, 2019 (Shift-I)

But-2-ene on reaction with alkaline KMnO4 at elevated temperature followed by

acidification will give :

A One molecule of CH3CHO and one molecule of CH3COOH

B CH3 – CH – CH – CH3

OH OH
C 2 molecules of CH3COOH

D 2 molecules of CH3CHO
12 April, 2023 (Shift-I)

(i) O3
2 – hexene (ii) H2O
Products

The two products formed in above reaction are

A Butanoic acid and acetic acid

B Butanal and acetic acid

C Butanal and acetaldehyde

D Butanoic acid and acetaldehyde

 O3
Zn / H2O

CH3
CH3
O3
Zn / H2O
No of pi Bonds & Hydrogenation
13 Jan, 2023 (Shift-II)

A hydrocarbon ‘X’ with formula C6H8 uses two moles of H2 on catalytic hydrogenation
of its one mole. On ozonolysis, ‘X’ yields tow moles of methane dicarbaldehyde. The
hydrocarbon ‘X’ is:

A Hexa-1, 3 , 5-triene

B 1-methylcyclopenta-1, 4-diene

C Cyclohexa-1, 3-diene

D Cyclohexa-1, 4-diene
 IIT-JEE-2012

The number of optically active products obtained from the complete ozonolysis of the
given compound is :
CH3 H

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

H CH3

A 0

B 1

C 2

D 4
 Benzene

Addition Reaction

Substitution Reaction

Cl — Cl AlCl3

R — Cl AlCl3

O
R — C — Cl AlCl3
 Electrophilic substitution reaction
1. Formation of sigma complex.

E+

2 . Loss of a proton gives the substitution product.

Rate of ESR :
 Reactivity Directing nature
Substituent groups
Effect on rate Effect on orientation
Very strongly
–O– , – NH- , – NHR , – NR2 , – OH Ortho-para directing
activating

Strongly activating Ortho-para directing

–OR , – NH – CO – R , – O – CO – R

–R , – Ar , – CH = CH2 Activating Ortho-para directing

 Reactivity Directing nature
Substituent groups
Effect on rate Effect on orientation

–X , – N = O , – CH2X , –CHX2 Deactivating Ortho-para directing

– CHO , – C – R , – COOH , Strongly

Meta directing
– COOR , – COCl , – C  N , – SO3H deactivating

Very strongly
–NO2 , –N+H3 , –N+R3 , – S+R2 , –CF3 Meta directing
deactivating
15 April, 2023 (Shift-I)

Decreasing order of reactivity towards electrophilic substitution for the following

compounds is :
CH3 OCH3
NMe2

a b CF3
d
c e

A c>b>a>d>e

B e>d>a>b>c

C a>d>e>b>c

D d>a>e>c>b
 Halogenation

(a) Br2 / FeBr3

(b) Br2 / Fe / Δ
(c) Cl2 / ZnCl2
(d) Cl2 / AlCl3

Cl2 / Fe
Heat

CH3

Cl2 / AlCl3
 I2 + AlCl3
Iodonation :

CH3O
Cl2
anhy AlCl3
O 2N
 For following sequence of reactions, the correct
31 Aug, 2021 (Shift-II)
products are :

1. Br2/Fe/
2. Mg/dry ether
3. CH3OH
Products

Br H CH3 OH
A + Mg B + Mg
OCH3 Br

H OCH3 OCH3
C + Mg D + HMgBr
Br
26 Aug, 2021 (Shift-II) Consider the given reaction, the Product A is:

O
Br2 , AlBr3
‘A’
(C2H5)2O (Major Product)

O Br O

A B
Br

O O

C D
Br

Br
Nitration
(a) Conc. HNO3 + Conc. H2SO4

(b) Fuming HNO3 / Conc. HNO3

CH3

Fuming HNO3
20 July, 2021 (Shift-II)

Benzene on nitration gives nitrobenzene in presence of HNO3 and H2SO4 mixture,

where :

A Both H2SO4 and HNO3 act as a bases

B Both H2SO4 and HNO3 act as an acids

C HNO3 acts as base and H2SO4 acts as an acid

D HNO3 acts as an acid and H2SO4 acts as a base

10 Jan, 2019 (Shift-II)

What will be the major product in the following mononitration reaction?

O HNO3
Conc. H2SO4
N
H

O O NO2
A B
N N
H H
NO2
O O2N
C D O
O 2N N N
H H
Sulphonation Conc. H2SO4

Oleum
Friedel Craft Reaction Alkylation :

AlCl3
R — Cl
01 Feb, 2023 (Shift-II)
+ HF X
 Major product

A B

D
C
10 April, 2023 (Shift-II)

The major product ‘P’ formed in the given reaction is:

CH3O Cl anhy
‘P’
AlCl3
(major)
O2N
CH3

CH3O CH3O
A B
O 2N O 2N CH3
CH3 CH3
CH3O NO3 CH3O
C D
O 2N OCH3 O2N
CH3 CH3 CH3
 Friedel Craft Reaction
Acylation :

O
R — C — Cl
AlCl3
Limitations :
(i) Poly alkylation is possible but poly acylation is not possible .
 (ii) Rearranged products may form in the Friedel Craft Alkylation reactions.

(iii) Highly reactive rings like aniline and highly deactivated rings like nitrobenzene ,
cyanobenzene do not give Friedel Craft reactions.
Preparation of benzene
Cyclic polymerisation of ethyne :

CH3 — C CH

Reduction of phenol : OH
Zn
08 Jan, 2020 (Shift-II)

In the following sequence of reactions the maximum number of atoms present in

molecule ‘C’ in one plane is

Red hot CH3Cl (1 eq)

A Cu tube
B Anhydrous AlCl3
C A is a lowest molecular weight alkyne
Addition reactions of benzene

H2 Ni
Heat

Cl2
Benzene hexachloride
500 K
BHC ( gammaxene)

Benzene on treatment with excess of chlorine in the presence of anhydrous AlCl3 can be
chlorinated to hexachlorobenzene (C6Cl6 ) .
Preparation of Alkane
(i) Li
Corey House Synthesis R — Cl
(ii) CuCl
(iii) R’ — Cl
 Soda – Lime Decarboxylation

O
NaOH CaO
CH3 C — OH Heat

O
C — OH

NaOH CaO
Heat
Kolbe Electrolysis

O
NaOH
CH3 C — OH
Electrolysis

NOTE : Methane cannot be prepared by this method

JEE Adv. 2019

Which of the following reactions produce (s) propane as a major product?

A H3C electrolysis
COONa + H2O

B H3C NaOH, CaO, 

COONa

C Cl Zn, dil. HCl

H3C

Br
Zn
D H3C Cl
Free Radical Substitution Reaction
UV Light or
R — H + X2
250° — 400°C

UV or temp.
(i) Chain initiation : X2 250° — 400°C

(ii) Chain propagation : X• + H – R

R• + X – X

(iii) Chain termination : X• + X•

R• + R•

R• + X•
Free radical allylic and benzylic substitution reaction
NBS = N-Bromosuccinimide

Cl2 / hv
CH3 – CH = CH2

CH3

NBS
10 Jan, 2019 (Shift-I)

Which hydrogen in compound (E) is easily replaceable during bromination reaction in

presence of light?
CH3 – CH2 – CH = CH2
   
A  - hydrogen

B  - hydrogen

C  - hydrogen

D  - hydrogen
26 Feb, 2021 (Shift-I)

For the given reaction :

CH2CH3
Br2
‘A’
UV light (major product)
monobrominated
CN
What is ‘A’?
Br CH3
CH2CH3 CH2CH3 CH CH2CH3
Br
A B C D
CN Br CN CN CN
Br
No of monochloro Products

Cl2
Heat

Cl2
Heat
JEE Mains 2022 / 26 July / Shift - II

Total number of isomers (including stereoisomers) obtained on

monochlorination of methylcyclohexane is __________.
06 April, 2023 (Shift-I)

Number of bromo derivatives obtained on treating ethane with excess of Br2, in

diffused sunlight is ………
 Rate of reaction of alkanes with halogens : F2 > Cl2 > Br2 > I2

Rate of replacement of hydrogens of alkanes : 3° > 2° > 1°

Fluorination is too violent to be controlled.

Iodination is very slow and a reversible reaction. It can be carried out in the presence
of oxidizing agents like HIO3 or HNO3 .
Reactivity Vs Selectivity
 Anhy. AlCl3
Isomerisation CH3(CH2)4CH3 HCl, 

13 April, 2023 (Shift-I) In the following reaction, ‘X’ is

Anhy. AlCl3
A CH3(CH2)4CH2Cl CH3(CH2)4CH3 ‘X’
HCl, 
Major Procut
B Cl – CH2 – (CH2)4 – CH2 – Cl

C CH3CH – (CH2)2 CH3

CH3
D
Aromatisation of Alkane :
25 Feb, 2021 (Shift-I)

Identify A in the given chemical reaction.

CH3 CH3 Mo2O3
773 K, 10-20 atm
‘A’
H2C major product
HC
H2C CH3
CH2

CH3
A B

CH3
C D
 Physical Properties

Boiling point Pentane hexane heptane

Boiling point n–Pentane Isopentane Neopentane

Shape approaches to spherical which results in decrease in vander Waal forces (as surface area decreases)
Melting Point :
Alkanes with odd carbon atoms have their carbon atom on the same side of the
molecule and in even carbon atom alkane the end carbon atom on opposite side.

Thus alkanes with even carbon atoms are packed closely in crystal lattice to permit greater intermolecular
attractions.

Physical State :
C1 to C4 & Neopentane : Gas

C5 to C17 : Colourless liquids

Above C17 : Waxy solids

06 Sept, 2020 (Shift-II)

The increasing order of the boiling points of the major products A, B and C of the
following reactions will be :
O

(C6H5CO)2
+ HBr A
(A)

(B) + HBr B

(B) + HBr C

A B<C<A B C<A<B

C A<B<C D A<C<B
Heat of Combustion

No of Carbon

Stability
09 Jan, 2020 (Shift-I)

The correct order of heat of combustion :

(a) (b) (c)

A (a) < (b) < (c)

B (a) < (c) < (b)

C (c) < (b) < (a)

D (b) < (c) < (a)

17 March, 2021 (Shift-I)

Mesityl oxide is a common name of : A 2,4-Dimethy lpentan-3 -one

B 3-Methylcyclohexanecarbaldehyde

C 2-Methylcyclohexanone

D 4-Methylpent-3-en-2-one

17 March, 2021 (Shift-II)

The total number of C – C sigma bonds in mesityl oxide (C6H10O) is _________. (Round off
to the nearest integer).