1ST TERM CHEMISTRY NOTES FOR SS3.

TOPICS:
1. INTRODUCTION TO ORGANIC CHEMISTRY
 Definition of Organic Chemistry
 Why organic compounds are many
 Sources of organic compounds
 General characteristics of organic compounds
 Classification of organic compounds
 Empirical formula.

2. IUPAC Nomenclature of organic compounds

3. BASIC CONCEPTS IN ORGANIC CHEMISTRY

 Functional groups
 Homologous series
 Isomerism
 Hydrocarbon radicals
 Saturated and Unsaturated compounds
 Types of organic reactions
 Bonding in organic chemistry
 Intermolecular forces
 Hybridization

4. ALKANES
 Sources
 General preparation
 Physical and chemical properties.
 Methane

5. ALKENES
 Sources
 General preparation
 Physical and chemical properties
 Ethene

6. ALKYNES
 Sources
 General preparation
 Physical and chemical properties
 Ethyne

7. ALKANOLS
 Classification of alcohols
 Physical and chemical properties
 Test for alcohols
 Methanol and phenols

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 1. INTRODUCTION TO ORGANIC CHEMISTRY
 Definition of Organic Chemistry
 Why organic compounds are many
 Sources of organic compounds
 General characteristics of organic compounds
 Classification of organic compounds
 Empirical formula.

Definition of Organic Chemistry

Organic chemistry is concerned with the chemistry of living materials or
substances that were at one time alive. These include plants, animals and
substances like coal and petroleum which are derived from plant and animal
remains. It is also concerned with chemistry of synthetic compounds i.e
compounds produced in the laboratory from inorganic sources.
All organic compounds whether or natural or synthetic contain the element
carbon.
Organic chemistry therefore, can be defined as chemistry of carbon
compounds.
Some carbon compounds are considered as inorganic compounds. These
include:
 Oxides of carbon
 Trioxocarbonates(IV)
 Hydrogen trioxocarbonate(IV)
 Metallic carbides
Carbons compounds which are studied in organic chemistry are those that
possess carbon to carbon bonds in their molecules.

Why organic compounds are many

The compounds of carbon are many compared with the compounds of any
other element. The ability of carbon to form large number of organic
compounds is due to the following reasons:

1. Ability of carbon to catenate

The variety and diversity of organic compounds is due to carbon atoms
having the ability to join with other carbon atoms to form carbon
chains. The chain may be straight, branched or cyclic. The property of
forming bonds with atoms of the same element
C
C C
C C C C C C C C C C
C C
Straight chain C C

Branched chain Cyclic chain

2. Tetravalent nature of carbon

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 Carbon has only two unpaired electrons in its ground state.

1s 2s 2px 2py 2pz

Ground state of carbon

Moreover, during chemical combination, the carbon atom acquires enough

energy to promote one of its 2s electrons to 2pz, thereby leaving four
unpaired electrons available for bonding. This allows carbon to form four
bonds with other elements.

1s 2s 2px 2py 2pz

Excited state of carbon

3. The ability of carbon to form multiple bonds

Carbon has the tendency of forming multiple bonds (double or triple)
with its own atoms or with atoms of other elements such as oxygen,
nitrogen etc.

C C C C C N
Double bond Triple bond Triple bond
btw carbon atoms btw carbon atoms btw carbon atom &
a nitrogen atom

4. The ability of carbon to form bonds with other elements

The ease with which carbon atoms form bonds with other elements
such as nitrogen, sulphur, halogen and oxygen is also responsible for
the large number of organic compounds.

Sources of organic compounds

The main sources of organic compounds are:
i. Plants and animals
ii. Coal
iii. Petroleum
iv. Natural gas

i. Plants and animals

Most organic compounds are obtained from plants and animals
sources. Organic compounds such as glucose, sucrose, maltose,
starch, cellulose fibres, latex, dyes, ethanol, protein, fats and oil are
obtained directly or indirectly from living organisms such as animals
and plants.

ii. Coal
Organic compounds such as benzene, toluene, phenol, naphthalene,
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 iii.Petroleum oil
Crude oil is a natural source of petrol, kerosene, diesel, lubricating
oil, Vaseline and asphalt or bitumen. These compounds are
separated by fractional distillation process.

iv. Natural gas

Compounds such as methane, propane and butane are constituents
of natural gas.

General characteristics of organic compounds

Organic compounds possess the following properties:
(i) Physical state
Organic compounds are covalent compounds with weak
intermolecular forces. They exist, at room temperature, as gases,
volatile liquids or low melting point solids.

(ii) Linkage
Organic compounds contain covalent bonds. The bonds are formed
when two or more electrons are shared between two atoms. The
bonds may single, double or triple.

(iii) Melting and boiling points

Organic compounds have low melting and boiling points and are
volatile in nature. Their low melting and boiling points is due to the
presence of weak intermolecular forces such as Vander Waal
forces and hydrogen bonds holding the molecules of these
compounds together.

(iv) Thermal stability

Organic compounds are less stable to heat compared to their
inorganic counterpart. They readily decompose on heating into
simpler molecules such as carbon(IV) oxide and water.

(v) Electrical conductivity

Organic compounds exist as covalent molecules. They do not
conduct electricity either in fused state or in solution. In other
words, they are non-electrolytes.

(vi) Solubility in water

Organic compounds are generally insoluble in water except for
those that possess polar groups such as –OH, –COOH, –SO 3H and –
NH2. Organic compounds with these groups dissolve in water by
forming hydrogen bonds with water molecules. Most organic
compounds are soluble in organic or non-polar solvents such as
tetrachloromethane, dichloromethane, ether and benzene.

(vii) Isomerism

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 A main characteristic of organic compounds is their tendency to
exhibit isomerism. This is a phenomenon whereby two or more
compounds may have the same formula but have different
properties.

(viii) Complex structure

Organic compounds have generally complex structures and very
large molecular masses.

(ix) Rate of reaction

Organic reactions generally proceed at much slower rates than
inorganic compounds. Because of this, most organic reaction
usually require heating, mixing or presence of catalyst before their
rate could be significantly increased.

Classification of organic compounds

Organic compound are classified on the basis of the similarity in their
structures. Generally they are divided into two categories.
 Aliphatic compounds
 Aromatic compound

Aliphatic compounds
These are compounds with short or long chains of carbon atoms. They
are subdivided into two categories according to the nature of their
carbon skeleton. These are:
i. Acyclic or open chain aliphatic
ii. Cyclic or closed chain aliphatic

Acyclic aliphatic compounds: These are compounds with open

chain of carbon atoms in their molecules. The carbon chain may be
either straight or branched chains. Examples:

C
C C
C C C C C C C C C C
C C
Straight chain C C

Branched chain Cyclic chain

Cyclic aliphatic compounds
Cyclic aliphatic compound possess closed chain or rings of atoms but
not benzene type in their molecules. They are also known as alicyclic
compounds. They are further divided into two categories namely:

i. Homocyclic or carbocyclic: These compounds contain rings

made up of the same atoms. E.g.
CH2
OR
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 H2C CH2
Cyclopropane

ii. Heterocyclic aliphatic compounds: These are aliphatic

compounds that contain one or more atoms other than carbon
atoms in their rings. E.g.
CH2 CH2

O
Ethylene oxide

Aromatic compounds
Benzene and compounds that resemble benzene in chemical behaviour
are called aromatic compounds. For a compound to be aromatic, it
must fulfill the following conditions:
- the compound must be cyclic in nature with one or more double
bonds in alternate positions
- the compound must take part in substitution reaction and resist
addition or oxidation.
- It must be flat and have tendency to show resonance.
Aromatic compounds are subdivided into two:
i. Benzenoids
ii. Non-benzenoids

 Benzenoids are aromatic compounds which contain in them

either one or more benzene rings fused together. E.g.
NH2

Benzene Nitrobenzene Naphthalene

 Non-bezenoids are aromatic compounds which do not contain
benzene rings. E.g.

O
Tripolene
IUPAC NOMENCLATURE OF ORGANIC COMPOUNDS
Under the IUPAC system, the name of an organic compound is determined
by:
(i) the structure of the principal chain of the compound.
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 (ii)The nature of the substituent(s) or side chain present in the
compound.
(iii) The nature of the functional group present in the compound.
The names of organic compounds under IUPAC system consists of Word
root, suffix and prefixes.

WORD ROOT
This is the name of the longest unbroken chain of carbon atoms in the
compound. If a compound has no side chain, the full name of such compound
can be derived by putting appropriate suffix to the word root of the
compound.
The table below shows the word root for chain containing 1 to 20 carbon
atoms.

NO OF CARBON WORD NO OF WORD

ATOMS ROOT CARBON ROOT
ATOMS
C = 1 Meth C = 11 Undec
C = 2 Eth C = 12 Dodec
C = 3 Prop C = 13 Tridec
C = 4 But C = 14 Tetradec
C = 5 Pent C = 15 Pentadec
C = 6 Hex C = 16 Hexadec
C = 7 Hept C = 17 Heptade
c
C=8 Oct C = 18 Octadec
C=9 Non C = 19 Nonadec
C = 10 Dec C = 20 Icos

SUFFIX
A suffix is placed after the root. A suffix may be primary or secondary. The
primary suffix indicates the nature of bonds in the carbon chain. In aliphatic
hydrocarbon, the primary suffixes are:
- “ane” for single bonded compounds
- “ene” for double bonded compounds
- “yne” for triple bonded compounds.

By adding the appropriate primary suffix to the word root, a complete name
of the compound can be obtained. For example in the compound below:

H H H H H

H C C C C C H

H H H H H
The word root is “Pent” and the suffix is “ane”
So the name of the compound is “Pent” + “ane” = Pentane

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Secondary suffix indicates the nature of the principal functional group in a
compound. Examples of secondary suffixes are listed below:

Compound Functional group Secondary

suffix
Alkanol - OH ol
Alkanal - CHO al
Alkanoic acid - COOH oic
Amides - CONH2 amide
Alkanoates - COOR oate
Amines - NH2 amine

Naming a compound with secondary suffix (functional groug)

In naming a compound containing a secondary suffix (i.e a compound with a

particular functional group), the terminal letter “e” of the primary suffix is
dropped if the secondary suffix begins with a vowel or preceded by the
prefix di or tri or tetra. For example the compound below is named as
follows:

H H H H H

H C C C C C OH

H H H H H
Chemical formula: C5H11OH or
CH3CH2CH2CH2CH2OH or
CH3(CH2)3 CH2OH
Word root = Pent (being 5 carbon atoms)
Primary suffix = ane
Secondary suffix = ol

Putting them together, (but the terminal letter “e” of primary suffix is
dropped)
We get:
Pent + an(e) + ol = Pentanol
In the same way, the compound below is named as follows:

H H H H O

H C C C C C

H H H H OH
Chemical formula: C5H9COOH or
CH3CH2CH2CH2COOH or
CH3(CH2)3 COOH
Word root = Pent (being 5 carbon atoms)
Primary suffix = ane

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Secondary suffix = oic

Putting them together, (but the terminal letter “e” of primary suffix is
dropped)
We get: Pent + an(e) + oic = Pentanoic.
For example the compound below with 2 functional groups is named as
follows:

H H H H H

H C C C C C H

H H OH OH H
Chemical formula: C5H10(OH)2 or
CH3CH2CH(OH)CH(OH)CH3 or

Word root = Pent (being 5 carbon atoms)

Primary suffix = ane
Secondary suffix = diol

Putting them together, (but the terminal letter “e” of primary suffix is
dropped)
We get:
Pent + an(e) + diol = Pentan-2,3-diol

THE PREFIX
A prefix is usually placed before the word root while naming an organic
compound. In organic chemistry, the following are used as prefixes.
i. Alkyl group: These are hydrocarbon radicals derived by the
removal of one hydrogen atom from alkane molecules. Below are
examples of alkyl group and their names.

Alkane Alkyl group Name

CH4 CH3– Methyl
C2H6 C2H5– Ethyl
C3H8 C2H7– propyl
C4H10 C4H9– Butyl
C5H12 C5H11– Pentyl etc

ii. Functional group

Some functional groups which are not regarded as the principal
functional group in a compound can be used as prefixes. E,g.

Functional group Name

–F Fluoro
–Cl Chloro
–Br Bromo
–I Iodo

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 –NO2 Nitro
–NH2 Amine
–OH Hydroxy
–OCH3 Methoxy
–CN Cyano
–OC2H5 Ethoxy etc

TOPIC: FUNCTIONAL GROUP

Most organic compounds consists of two parts. The first part is the carbon-
hydrogen framework while the second part is the functional group. The carbon-
hydrogen frame work of the molecule affects the physical properties such as
melting point, boiling point, solubility, density etc. the functional group on the other
hands, determines the chemical properties of the compound. For example, the
presence of amino group in amine impact a basic character to the amines. Likewise,
the presence of carboxylic acid impart acidic character to the group.

A functional group can therefore be defined as an atom, group of atoms or

chemical bonds present in a molecule which largely determines its
chemical properties.

All organic compounds containing the same functional group show similar chemical
reactions. For example, all compounds with –COOH group react with alkanols to
form esters.

RCOOH + R’OH RCOOR’ H2O

Organic compound may contain more than one functional group. For example, an
amino acid molecule contains two functional groups; an amino group (–HN2) and a
carboxylic acid group (–COOH). Similarly, a lactic acid molecule contains two
functional groups; a hydroxyl group (–OH) and a carboxylic acid group (–COOH)

Class of compounds Name of functional Structure of functional

group group
Alkenes Double bond C=C
Alkynes Triple bond C C
Haloalkanes Halogen -X where x can be F, Cl, Br, I
Alcohols Hydroxyl -OH
Alkanals (Aldehydes) Aldehydic -CHO O

C
Alkanones (Ketones) Ketonic =CO

C O

Carboxylic acid Carboxyl -COOH,

O

C O H
Alkanoates (Ester) Ester -COOR
O

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 C O R’

TOPIC: HOMOLOGOUS SERIES

Organic compounds are classified into different families according to their functional
groups. Each family contains series of compounds that share the same chemical
properties. The members of a given family are called Homologues of the family.
Each homologue differs from the preceding one by a CH 2 group.
An homologous series can therefore be defined as a group of compounds
having the same functional group and similar chemical properties in which
successive members differ in composition by one or several CH2 group.

This phenomenon is called Homology

Characteristics of homologous series.

The following are the common characteristics of the members present in a given
homologous series.

1. They have the same general method of preparation.

Homologues of the same series are prepared by the same general method.
For example, each member of the alkanes series is prepared by heating
appropriate sodium alkanoate with soda lime. Methane is prepared by
heating sodium ethanoate with soda lime
CH3COONa(s) + NaOH CH4(g) + Na2CO3(s)

2. They have the same chemical properties.

The members of homologous series share the same chemical properties. For
example, all members of alkenes undergo addition reactions.

3. They have different physical properties.

The physical properties such as density, melting point, boiling point of the
members of an homologous series show a regular gradation with rise in
molecular mass.

4. They have the same functional group.

The members of an homologous series have the same functional group. For
example, the alkanols have hydroxyl as their functional group.

5. They have the same difference in composition.

Successive members of an homologous series differ in composition by a CH2
group. That is the difference in molecular mass of successive homologues is
14.

The table below shows some homologous series.

Homologous General formula Example
series
Alkanes CnH2n+2 Methane
Alkenes CnH2n Ethane
Alkynes CnH2n-2 Ethyne

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 Alkanols CnH2n+1OH, or ROH Ethanol
Haloalkanes CnH2n+1 X, or RX Chloromethan
e
Alkanals CnH2n+1 CHO, or RCHO Ethanal
Alkanones CnH2n+1 CO CnH2n+1, or RCOR Propan-2-one
Carboxylic acids CnH2n+1COOH or RCOOH Ethanoic acid
Alkanoates (Ester) CnH2n+1COO CnH2n+1 or Ethylethanoat
RCOOR’ e
Amides CnH2n+1CONH2 or RCOOHN2 Ethanamide

TOPIC: ISOMERISM
The word “Isomerism” is derived from two Greek words;
 Isos meaning equal
 Meros meaning part

Isomerism can be defined as the existence of two or more organic

compounds havimg the same molecular formula but different
properties.

Molecules that have the same kind and number of atoms but different
properties are called Isomers.

Isomerism is divided into two main types namely;

i. Structural isomerism
ii. Stereo isomerism.

Structural isomerism is further divided into chain isomerism, position

isomerism, functional isomerism and ring chain isomerism. On the
other hand, Stereo isomerism is further divided into geometric
isomerism and optical isomerism.

Chart showing the summary of types of isomerism

Isomerism

Structural Stereo
Isomerism
Isomerism

Chain Position Functional Ring-chain Geometric Optical

Isomerism Isomerism Isomerism Isomerism Isomerism
Isomerism

STRUCTURAL ISOMERISM
Structural isomerism can be defined as existence of two or more compounds
with the same molecular formula but different structures.
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Structural isomers have
i. the same molecular formula
ii. different structural formula
iii. different properties and the number of structural isomers increases as
molecular mass increases.

Chain isomerism
This can be defined as the existence of compounds having the same
molecular formula but different arrangement of carbon chain within the
molecule.
In this type of isomerism, isomers differ from one another in the
arrangement of carbon chain or skeleton. It’s also known as Nuclear
isomerism.

For example the molecular formula C4H10 has two chain isomers. These are
shown below:

C C C C C C C
Continuous chain
C
Branched chain
Position isomerism
This can be defined as the existence of compounds having the same
molecular formula but different arrangement of atoms within the molecule.
For example, Propan-1-ol and propan-2-ol are two positional isomers of
Propanol

H H H H H H

H C C C OH H C C C H

H H H H OH H
Propan-1-ol Propan-2-ol

Other examples of positional isomers are:

 But-1-ene and But-2-ene
 But-1-yne and But-2-yne e.t.c

Functional group isomerism

Functional group isomerism is the existence of compounds having the same
molecular formula but different functional groups.
In this type of isomerism, the isomers have the same carbon skeleton but
different functional groups. Functional group isomers therefore, belong to
different homologous series.
For example, ethanol and methoxymethane are functional group isomers.
Both compounds have the molecular formula (C2H6O) but different functional
groups. Ethanol has hydroxyl group (-OH) and methoxyethane has alkoxy or
ether (-O-) group.

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 H H H H

H C O C H H C C OH

H H H H
Methoxymetane Ethanol
(Functional group is – O –) (Functional group is – OH)

Other examples of functional isomers are:

 Propanal and Propan-2-one
 Ethanoic acid and Methylmethanoate e.t.c
Ring chain isomerism
This is existence of compounds having the same molecular formula but
possessing open chain and cyclic structures. Examples

CH3CH CH2 and

Prop-1-ene Cyclopropane
Both have molecular formula C3H6
Other examples of ring chain isomers are:

CH3CH2CH CH2 and

But-1-ene Cyclobutane
Both have molecular formula C4H8

CH3C CH2 and

Prop-1-yne Cyclopropene
Both have molecular formula C3H4

STEREO ISOMERISM
Stereo isomerism deals with molecules that have the same order of
attachment of the atoms, but different arrangement of atoms in space.
Stereo isomerism is sub divided into Geometric isomerism and Optical
isomerism.

Geometrical isomerism
This can be defined as the existence of organic compounds with the same
structural formula but difference in the spatial arrangement of atoms or
groups of atoms about the double bond.
It is also known as cis-trans isomerism. Geometrical isomerism is
exhibited by certain members of the alkene family.
For a compound to exhibit geometrical isomerism, it must satisfy the
following conditions;
i. The molecule must have a double bond
ii. The atoms or group of atoms attached to each of the double bonded
carbon atoms must be different.

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Geometrical isomerism occurs in some members of the alkene family
because rotation of atoms or group of atoms at carbon-carbon double bond
is restricted. Thus, alkenes which have different groups attached to the same
carbon exhibit two space isomers called Geometrical isomers or cis-trans
isomers.

A cis-isomer is one with identical atoms or group of atoms on the same sides
of the double bond. Eg
X Y CH3 CH3

C C eg C C

Z Z H H
Cis-isomer Cis-But-2-ene
A trans-isomer is one with the atoms or group of atoms on the opposite sides
of the double bond.
X Z CH3 H

C C eg C C

Z X H CH3
Trans-isomer Trans-But-2-ene

Other geometrical isomers are;

Br Br Br H

C C and C C

H H H Br
cis-1,2-dibromoethene Trans-1,2-dibromoethene

H COOH HOOC H

C C
and

C C

H COOH H COOH
cis-But-2-ene-1,4-dioic acid Trans-But-2-ene-1,4-dioic acid

Optical isomerism
Optical isomerism is a type of stereoisomerism in which the isomers differ in
the spatial arrangement of the atom or group of atoms. A molecule exhibits
optical isomerism if it cannot be superimposed on its mirror image. That is
the compound cannot be placed directly on its mirror image so that the

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corresponding atoms overlap. For example, left hand is a mirror image of the
right hand and cannot be superimposed on each other.

Molecules that cannot be superimposed on their mirror images are said to be

chiral molecules while those that can be superimposed on their mirror
images are said to be achiral.

Molecules that will exhibit optical isomerism must contain an asymmetrical

carbon atom.

A carbon atom is said to be asymmetrical if it is joined to four different

atoms or groups. A compound containing one chiral centre can exist in two
forms that are non-superimposed mirror image of each other. These two
isomeric forms are called optical isomers or enantiomers.
For example 3-methyhexane is structural represented as follows:

CH3 CH2 CH CH2 CH2 CH3

CH3
The carbon number 3 has four different groups attached to it, it is therefore
an asymmetric carbon. This means that 3-methyhexane can exhibit optical
isomerism.
On the other hand, 2-chloro,2-methypentane below doesn’t have
asymmetric carbon atom hence, cannot exhibit optical isomerism.
Cl

CH3 CH CH2 CH2 CH3

CH3
Optical isomers of 3-methyhexane and 2-chloro,2-methypentane
3-methyhexane
CH3 CH2 CH CH2 CH2 CH3

CH3
H Mirror H

C C

C2H5 C3H7 C3H7 C2H5

CH3 CH3

2-chloro,2-methypentane
Cl

CH3 CH CH2 CH2 CH3

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 CH3

H Mirror H

C C

C2H5 CH3 H3C C2H5

Cl Cl

Characteristics of optical isomers

1. Optical isomers rotate plane polarized light. One isomer rotates plane
polarized light to the left and the other to the right. The isomer that
rotates it to the right is represented as d-(dextro-rotary) or (+) while
the one that rotates to the left is represented as l-(laevo-rotary) (-).
2. The chemical properties of optical isomers tend to be similar, though
the rates of their reactions may differ.
3. A mixture of equal concentrations of both (+) and (-) forms a mixture
called racemic mixture.
4. A racemic mixture has no effect on plane polarized light since both
enantiomers have an equal and opposite effect.
5. The process of separating one isomer from the other is called
resolution.

HYDROCARBON RADICALS
When one hydrogen atom is removed from an aliphatic or aromatic
hydrocarbon molecules, the resulting molecule becomes a hydrocarbon
radical. Among the hydrocarbon radicals are;
- Alkyl group
- Alkenyl group
- Alkynyl group
- Phenyl group.

Alkyl Group
This hydrocarbon radical is derived by the removal of one hydrogen atom
from an alkane. Alkyl groups are usually represented by the symbol R. The
general formula of alkyl group is given as CnH2n+1 where n is the number of
carbon atoms in one molecule of the alkane. Their names are derived by
replacing the ‘ane’ of corresponding alkane by the suffix ‘yl’

Table showing some examples of alkyl and their names

Alkane Name Alkyl group Name
CH4 Methane CH3- Methyl
CH3-CH3 Ethane CH3-CH2- Ethyl

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CH3-CH2-CH3 Propane CH3-CH2-CH2- Propyl
CH3-CH2-CH2-CH3 Butane CH3-CH2-CH2-CH2- Butyl
CH3-CH2-CH2-CH2-CH3 Pentane CH3-CH2-CH2-CH2-CH2- Pentyl

Alkenyl
This group is obtained by the removal of one hydrogen atom from alkenes.
Their names are derived by replacing the ‘e’ of corresponding alkane by the
suffix ‘yl’

Table showing some examples of alkenyl and their names

Alkene Name Alkenyl group Name
CH2 CH2 Ethene CH2 CH- Ethenyl (Vinyl)
CH2 CH-CH3 Propen CH2 CH-CH2- Propenyl
e
CH2 CH-CH2-CH3 Butene CH2 CH2-CH2-CH2- Butenyl
CH2 CH-CH2-CH2-CH3 Penten CH2 CH2-CH2-CH2-CH2- Pentenyl
e
Alkynyl
This group is obtained by the removal of one hydrogen atom from alkynes.
Their names are derived by replacing the ‘e’ of corresponding alkane by the
suffix ‘yl’

Table showing some examples of alkynyl and their names

Alkyne Name Alkynyl group Name
CH CH Ethene HC C- Ethynyl
CH C-CH3 Propen HC C-CH2- Propynyl
e
CH C-CH2-CH3 Butene HC C-CH2-CH2- Butynyl

Phenyl group
A phenyl group is an hydrocarbon radical obtained by the removing one
hydrogen atom from benzene nucleus. The formula of phenyl group is (–
C6H5).
Below are the structures of phenyl groups.

or or

Structures of phenyl group

Saturated and Unsaturated compounds

An organic compound in which all the atoms have four single covalent
bonds is called Saturated compound.
An organic compound containing one or more multiple (double or triple)
covalent bonds is to be unsaturated. E.g.
H H H H

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H C C H H C C H

H H
Saturated compound Unsaturated compound
(containing one double bond)

Types of organic reactions

There are many types of organic reaction. These include:

1. Substitution reaction
A substitution reaction is one which involves the direct replacement of
an atom or group of atoms in a molecule by another atom or group of
atoms.

H H

H C X + Y H C Y + X

H H

A substitution reaction in which the attacking reagent is an

Electrophile is called Electrophilic substitution. This type of
substitution reaction is common in benzene and other aromatic
compounds.

+ Cl2 Cl + HCl

A substitution reaction in which the attacking reagent is a

Nucleophile is known as Nucleophilic substitution. This type of
substitution is common with haloalkanes (alkyl halides).

H H

H C Br + KOH H C OH + KBr

H H

2. Addition reaction
This is a reaction in which two molecules react to form a single
product. Addition reaction usually takes place in unsaturated
compounds. In this reaction, the multiple bonds eventually change to
single bonds. E.g.
H H H H

H C C H+ X Y H C C H
(Attacking reagent)
X Y
Unsaturated ethene Saturated product
[Type text]
 3. Elimination reaction
This is a reaction in which a small molecule is removed from adjacent
carbon atoms of an organic compound resulting in the formation of
multiple bond. Elimination reaction is opposite of addition reaction.
Examples of elimination include:

i. Dehydration : This is the removal of a molecule of water

from a reagent.

H H H H
Conc. H2SO4
H C C H H C C H + H2O

H OH

ii. Dehydrohalogenation : This is the removal of hydrogen

halides from a reactant.
H H H H
Alcohol
H C C H + KOH H C C H + KBr + H2O

H Br
iii.Fragmentation or decomposition : This is a more
complicated form of elimination reaction. An example is
cracking or breaking down of large molecules in petroleum
fractions into smaller ones by heat, pressure and catalyst.
E.g.
CH3(CH2)10CH3 CH3(CH2)7CH3 + CH3CH CH2
4. Rearrangement reactions
A rearrangement reaction is one in which a change in position of some
atoms or group of atoms take place. Example of such reaction is
isomerism where one substance is changed into its isomer.

CH3CH2CH2CH3 CH3CHCH3

CH3

5. Condensation reactions:
A condensation reaction is one in which two or more molecules of the
same or different reactants combine to form a product with the
elimination of simple molecules such as water, HCl, ammonia etc.

This type of reaction is illustrated below

A H + HO B A B + H2O

A H + Cl B A B + HCl

[Type text]
 6. Polymerization reactions:
These reactions involve the union of large number of smaller molecules
called monomers to form a molecule with high molecular mass called
polymer. For example

nCH2 CH2 ( CH2 CH2 )n

monomer polymer

ALKANES
The alkanes are hydrocarbons in which the carbon atoms are linked by
single covalent bonds. They form a homologous series having the general
formula CnH2n+1 where n may have the value of 1,2,3…… The simplest
alkane is methane. Below are structures of simple alkanes.
H H H H H H

H C H ; H C C H ; H C C C H

H H H H H H
Methane Ethane Propane
Sources of alkanes
Alkanes are wide spread in nature. They are present in petroleum and
natural gas. Lower alkanes such as methane, ethane, propane and butane
are components of natural gas. Heavier alkanes are found in kerosene,
lubricating oil and in paraffin used to make candles. Solid alkanes are the
main components bitumen, asphalts and mineral wax.

General preparation of alkanes

Alkanes are prepared by the following general methods

1. Catalytic hydrogenation of unsaturated hydrocarbons;

When hydrogen gas is passed through an alkene or alkyne in the
presence of nickel, palladium or platinium catalyst at a high
temperature and pressure, alkane is formed.
H H H H

H C C H + H H Pt/Ni/Pd
H C C H
Ethene (an alkene)
H H
Ethane (an alkane)
2. Reduction of alkylhalides
Alkylhalides (haloalkanes) are reduced to alkanes by using suitable reducing
agents. For example;
Zn/HCl
R X + 2[H] R H + HX
Alkylhalide Alkane

Where X may be chlorine, bromine, iodine or fluorine

[Type text]
 E.g. CH3CH2Br + 2[H] Zn/HCl
CH3CH3 + HBr

3. Decarboxylation reaction
Alkane is formed when sodium alkanoate is heated with soda-lime
(mixture of NaOH and CaO at about 3570C)

RCOONa(s) + NaOH(aq) Cao/Heat

R H + Na2CO3(aq)
Sodium alkanoate Alkane

CH3COONa(s) + NaOH(aq) Cao/Heat

CH4(g) + Na2CO3(s)
Sodium ethanoate Methane

Physical properties of alkanes

1. Physical state
Alkanes having one to four carbon atoms per molecule are gases,
those having five to seventeen carbon atoms are liquids while the
rest are solids at room temperature.

2. Melting and boiling point

The melting and boiling points of alkanes increase with increase in
molecular mass. Branching in alkanes lowers the melting and
boiling points. As a result, branched isomers have lower melting and
boiling points than their straight chain counterparts.

3. Solubility
The alkanes are non-polar molecules. They are therefore insoluble
in polar solvent like water but soluble in non-polar solvents like
benzene, ether and tetrachloromethane.

4. Density
The density of alkanes increases with molecular mass. Branching
also lowers the density of alkanes.

Chemical properties of the alkanes

Alkanes are inert. At ordinary temperature, they do not react with
reagents such as bromine water, potassium tetraoxomanganate(VII)
solution and other oxidizing agents. This is the reason they are
referred to as paraffin. However, alkanes do undergo combustion and
substitution reactions.

Combustion
All alkanes burn in air or excess oxygen with non-smoky flame
forming carbon(IV)oxide and water. A lot of heat is produced in the
process. The combustion of alkanes can be represented by the general
formula below.

[Type text]
 C n H 2 n +2+ ( 3 n+1
2 )
O n CO + ( n+1 ) H O
2 2 2

For example when n=1, that Methane

C 1 H (2 × 1)+2 +( (3 ×1)+
2
1
)O 1CO +( 1+1) H O
2 2 2

CH 4 (g) +2 O2(g ) CO 2(g )+ 2 H 2 O(g)

Incomplete combustion
If the combustion takes place in the limited supply of air or oxygen, a
soot or carbon black is formed. This is due to the presence of un-burnt
carbon particles. The carbon black formed is commonly used in the
manufacture of black ink, paint and polishes.

CH 4 (g) +O2 (g) C(s) + H 2 O(g )

Substitution reaction
Alkanes undergo substitution reaction with halogen to form
haloalkanes. This reaction is called Halogenation of alkanes. It takes
place under the influence of ultraviolet light or at high temperature.
The reaction is called chlorination if the halogen is chlorine and
bromination if it is bromine.

The chlorination of alkane can be represented by the general formula

below:

R H + Cl Cl light
R Cl + H Cl

Where R is an alkyl group

Chlorination of methane
In the presence of light or high temperature, methane reacts
vigorously with chlorine to yield chloromethane and hydrogen chloride.

CH4(g) + Cl2(g) light

CH3Cl(g) + HCl(g)
H H

H C H + Cl Cl light
H C Cl + H Cl

H H
Methane Chloromethane
With more chlorine molecules, all the hydrogen atoms of methane may
be substituted to give rise to a number of other compounds.

CH3Cl(g) + Cl2(g) light

CH2Cl2(g) + HCl(g)
H H
[Type text]
 H C H + Cl Cl light
H C Cl + H Cl

Cl Cl
Chloromethane Dichloromethane

CH2Cl2(g) + Cl2(g) light

CHCl3(g) + HCl(g)
H H

H C Cl + Cl Cl light
Cl C Cl + H Cl

Cl Cl
Dichloromethane Trichloromethane

CHCl3(g) + Cl2(g) light

CCl4(g) + HCl(g)
H Cl

Cl C Cl + Cl Cl light
Cl C Cl + H Cl

Cl Cl
Trichloromethane Tetrachloromethane
Note that bromine also reacts with methane in the same way but less readily
than chlorine. The reaction with fluorine is explosive even in the dark and at
room temperature.

METHANE
Methane is the simplest member of the alkanes. It is commercially found in
nature wherever bacteria decompose organic matter in the absence of air
that is marshes or swarmps and this is the reason, it is called Marsh gas.
Methane also occurs as fire damp in coalmine. When mixed with 5% to 14%
of air, it is explosive. It is also a product of dry distillation of wood, peat and
coal. It is contained in natural gas and illuminating gas. (An illuminating
gas is a mixture of combustible gases, mainly methane and
hydrogen that is formed during the thermal processing of coal.)

Laboratory preparation of Methane

Methane is prepared in the laboratory by heating a mixture of Sodium
ethanote and soda-lime in the ratio of 1:1 by mass. Calcium oxide is added
to sodium hydroxide to make it non-deliquescent. The mixture is heated in a
hard glass tube gently first and then strongly. Methane is formed which is
collected over water.

Equation for the reaction:

[Type text]
CH3COONa(aq) + NaOH(aq) CH4(g) + Na2CO3(s)

Physical properties of methane

1. Methane is colourless, odourless and tasteless
2. It is less dense than air
3. It is slightly soluble in water
4. It is neutral to litmus paper.
Uses of methane
1. It is used as fuel
2. It is used for the production of valuable substances such as carbon
black, chloroform and tetrachloromethane.
3. It is used for the production of synthesis gas.

ALKENES
Alkenes are unsaturated hydrocarbons containing at least one carbon –
carbon double bond. They form a homologous series having the general
formula CnH2n where n is the number of carbon atoms per molecule of
alkene. The simplest alkene is the Ethene. Other simple alkenes include
propene and butane.
H H H

C C H C C C H

H H H H H
Ethene Prop-1-ene
H

H C C C C H

H H H H
But-1-ene

Sources of alkenes

[Type text]
In nature, alkenes are present in petroleum, natural gas as well as coal gas.
Alkenes are produced in large amount by the cracking of high boiling
hydrocarbon fractions of petroleum.

General preparation of alkenes.

Alkenes are prepared by the following general methods
1. Dehydration of alkanols
An alkanol is converted to alkene by the elimination of water molecule
(dehydration). This process can be carried out by heating alkanol with
tetraoxosulphate(VI) acid at about 2000C or by passing alkanol vapour
over aluminium oxide (Al2O3) at about 3500C – 4500C.
H H H H

H 3 PO 4 ∨H 2 SO 4
H C C H 0 0 C C + H2O
350 C−450 C

H OH H H

2. Dehydrohalogenation.
This process the elimination of hydrogen halide from haloalkanes
(alkylhalides). The process is achieved by treating the alkylhalide with
alcoholic solution of potassium hydroxide.
For example
H H H H H H

H C C C Cl KOH
H C C C H + HCl

H H H H
Chloropropane Propene

3. Cracking of petroleum
Alkenes are produced commercially by the thermal cracking of long
chain petroleum fractions.

Higher alkane Smaller alkane + alkene

Physical properties of alkenes

1. Physical state: The first four members of alkene series exist as
colourless gases at room temperature. Alkenes having five to eighteen
carbon atoms are liquids while the rest are solids.
2. Smell: Except ethane which has a pleasant smell, all other alkenes are
odourless gases.
3. Melting and boiling points: In general, alkenes have higher melting
and boiling points than the corresponding alkanes and these values
increase with increase in molecular mass of the alkene. Alkenes with
double bonds at the terminal carbon atoms usually have lower boiling
points than corresponding alkenes with double bond in the middle.
[Type text]
 4. Solubility: Alkenes are insoluble in water because they are non-polar.
They are however soluble in organic solvents like benzene, ethanol,
ether and tetrachloromethane.

Chemical properties of alkenes

The alkenes are much more reactive than the alkanes. The reactions of
alkenes include: combustion, addition, oxidation and polymerization.

1. Combustion of alkenes
Alkenes burn in excess air or oxygen with sooty flame to form
carbon(IV)oxide and water. The reaction is highly exothermic in nature
and the heat evolved is used for welding purposes. The flame is called
oxy-ethylene flame. The combustion of alkenes can be represented
by the general formula below.

Cn H2n+ ( 32n )O n CO +n H O
2 2 2

For example when n=2, that is ethene

C 2 H 2 ×2 + ( 3 ×2 2 )O 2 CO +2 H O
2 2 2

C2H4(g) + 3O2(g) 2CO2(g) + 2H2O(l)

2. Addition reactions
Alkenes, because of the carbon – carbon double bonds in their
molecules, generally undergo addition reactions. During the
reaction, the double bond in alkenes is converted to single bond by
the addition of an attacking reagent. Alkenes undergo a number of
additions. These include:
i. Addition of hydrogen: In presence of finely divided nickel,
platinum or palladium catalyst, hydrogen gas is added across the
double bond of alkenes to form the corresponding alkanes. This
reaction is called catalytic hydrogenation of alkenes.
E.g.
H H H H

C C + H H H C C H

H H H H

ii. Addition of halogen: Halogen such as chlorine, bromine or

iodine reacts readily with alkenes to form 1,2-dihaloalkane. This
reaction takes place in the presence of an inert solvent such as
tetrachloromethane (CCl4). The reaction with fluorine is explosive

[Type text]
 while iodine has little tendency to react with alkenes. The order
of addition reaction of halogen to alkenes is
Fluorine > Chlorine > Bromine > Iodine
E.g
H H H H

C C + Br Br H C C H

H H H H

NOTE: If the alkenes is not symmetrical that is the double bond is not at
equal distance between the two carbon ends, the halogen atom goes to the
carbon with smaller number of hydrogen atom while the hydrogen atom of
the attacking reagent goes to the carbon with more hydrogen atoms. This is
known as Markornikoff’s rule.
E.g.

H H H H H H

H C C C H+ H Br H C C C H
(Hydrogen bromide)
H H Br H
Prop-1-ene 2-
Bromopropane
(Unsymmetrical alkene)

iii. Addition of bromine water: Bromine dissolves in water to

form a solution known as Bromine water.
H2O(l) + Br2(s) BrOH(l) + HBr(g)

The bromine water reacts readily with alkene at room

temperature to form Bromoalkanol. For example:
E.g
H H OH Br

C C + HO Br H C C H

H H H H
Ethene 2-bromoethanol
The reddish brown colour of this solution disappears as the
addition product is formed. This can also be used to test for
unsaturation.

iv. Addition of water: in the presence of acid catalyst, alkenes can

be hydrated to form alkanols. The reaction takes place at room
temperature.
E.g
H H H OH
[Type text]
 C C + H OH H C C H

H H H H
Ethene Ethanol

3. Oxidation with KMnO4

Alkenes react with dilute alkaline or acidified potassium
tetraoxomamganate(VII) solution (Bayer’s reagent) to form
ethane-1,2-diol (ethylene glycol). This reaction is called
Hydroxylation reaction since during this reaction, two hydroxyl
groups are added across the double bonds. For example; E.g
H H OH OH
+¿
H
C C + H2O+[O] ¿ H C C
KMnO 4
H

H H H H
Ethene Ethan-1,2-diol
The purple colour of the reagent turns colourless if the solution is
acidic or green if the solution is alkaline. The reaction is also used to
test for unsaturation.

4. Catalytic oxidation
Alkenes react with oxygen in the presence of silver catalyst to form
epoxyalkanes or epoxides. The reaction takes place at 3200C.
E.g
H H O
+¿
Ag
C C + ½O2 0
¿ H C C H
320 C

H H H H
Ethene Epoxyethane

5. Reaction with ozone

When ozone is passed through a solution of alkene in the presence
of inert solvent like CCl4 at low temperature, it oxidizes alkenes to
ozonides.
E.g
H H O

C C + O3 CCl 4 H C C H

H H H O O H
Ethene Ethene ozonide

[Type text]
 6. Polymerization reaction
This is a process in which simple molecules combine to form
compounds of higher molecular mass. This reaction is common to
compounds containing double or triple bonds.
Polymerization of ethene
When ethene is heated in the presence of oxygen at 2000C – 4000C
under high pressure, polythene is formed.
0 0
200 C−400 C / pressure
nCH2 CH2 (CH2 CH2)n
O2 initiator

Uses of ethene
1. Ethene is used in the manufacture of ethanol and ethan –1,2–
diol.
2. It is used in the preparation of synthetic fibre e.g terylene
3. It is used in the manufacture of plastics e.g polyethene.
4. It is used in the ripening of fruits

ALKYNES
Alkynes are unsaturated hydrocarbons containing at least one carbon –
carbon triple bond. They form a homologous series having the general
formula CnH2n–2 where n is the number of carbon atoms per molecule of
alkyne. The simplest alkyne is the Ethyne. Other simple alkynes include
propyne and butyne.

H C C H H
Ethyne
H C C C H
Prop-1-yne
H H H

H C C C C H

H H But-1-yne

Classification of alkynes
Alkynes are classified into two:
i. Terminal alkynes: In these alkynes, the triple bond is at the end of
the chain. Eg.
H

H C C C H
Prop-1-yne
H

H H
[Type text]
H C C C C H

H H But-1-yne

ii. Non-terminal alkynes: In these alkynes, the triple bond is within the
chain. Eg.

H H H H H

H C C C C H ; H C C C C C H

H H H H H
But-2-yne Pent-2-yne

Preparation of alkynes
Alkynes are prepared by the following general methods.
1. Action of water on calcium dicarbide
Ethyne is prepared in the laboratory by the action of water on calcium
dicarbide. This method can also be used to prepare alkyne on
commercial scale.

CaC2(s) + 2H2O(l) HC CH + Ca(OH)2(aq)

2. Dehalogenation of tetrahalides;
The removal of halogen atoms from a tetrahalide gives a triple bond.
This can be achieved by treating alkylhalides with zinc in the presence
of alcohol.
Br Br

2 Zn
R C C R R C C R + 2ZnBr2
alcohol
Alkyne
Br Br
Tetrahalide (where R may H or alkyl group)

3. Dehydrohalogenation of dihalide:
An alkyne is formed when two molecules of hydrogen halides are
eliminated from adjacent carbon atoms in a dihalide. This can be
achieved with concentrated alcoholic potassium hydroxide.
Br Br

R C C R + 2KOH(aq) R C C R + 2KBr(aq) +
2H2O(l)

H H (where R may H or alkyl group)

[Type text]
Physical properties of alkynes
1. Physical state: Ethye, propyne and butyne are colourless gases at
room temperature. The alkyne with five to thirteen carbon atoms are
liquid while the rest are solid at room temperature.
2. Density: Like the alkanes and alkenes, the density of alkynes
increases with increase with increase in molecular mass. Ethyne is
slightly less dense than water. It is easily converted to liquid which
boils at –83.60C.
3. Melting and boiling points: In general, alkynes have higher melting
and boiling points than the corresponding alkanes and alkenes. The
melting and boiling increase with increase in molecular mass of the
alkynes.
4. Solubility: Alkynes are almost insoluble in water but dissolve readily
in organic solvents like benzene, ethanol, ether, ethanone etc.

Chemical properties of alkynes

1. Combustion of alkynes
Alkynes burn in excess air or oxygen to form carbon(IV)oxide and
water. The reaction is highly exothermic in nature. The combustion of
alkenes can be represented by the general formula below.

C n H 2 n−2 + ( 3 n−1
2 )
O n CO +(n−1) H O
2 2 2

For example when n=2, that is ethyne

( ( 3 ×22)−1 )O 2CO + H O
C 2 H ( 2× 2)−2 + 2 2 2

C2H2(g) + ( 52 )O2(g) 2CO2(g) + H2O(l)

2. Addition reactions
The addition reactions of alkynes involve two molecules of the
attacking reagents converting triple bond first to double and then
single bond.

X X X X

C C + X2 C C + X2 C C
Double bond
X X
Single bond
The following are the addition reactions of alkynes:
(a) Addition of hydrogen:
In the presence of nickel or platinum or palladium catalyst, alkyne
readily react with hydrogen. This reaction is called Catalytic
hydrogenation of alkyne.
[Type text]
 H H H H

H C C H + H2 H C C H + H2 H C C H
Double bond
H H
Single bond
(b)Addition of halogen:
Halogen such as chlorine or bromine reacts with alkynes in the
presence of metallic halide catalyst or tetrachloromethane to form
tetrahalide. For example:

Cl Cl Cl Cl

H C C H + Cl2 H C C H + Cl2 H C C H
Ethyne 1,2-dichloroethene
Cl Cl
Tetrachloroethane
(c) Addition of hydrogen halide:
Hydrogen halides such as HCl or HBr or HI reacts with alkyne to
form a saturated product. HBr and HI react more readily with alkyne
than HCl. The reaction occurs in the presence of light or metallic
catalyst.
H Br H Br

H C C H + HBr H C C H + HBr H C C H
Ethyne Bromoethene
H Br
1,1-dibromoethane

(d)Addition of chlorine or bromine water:

Alkynes react with chlorine or bromine water (HOCI and HOBr) to
form dihaloalkanal. For example
OH Br Br

H C C H + HOBr H C C H + HOBr H C C
H+H2O
Ethyne 2-bromoethenol
O Br
2,2-dibromoethanal

(e) Reaction with water:

Alkynes react with water in the presence of mercury
tetraoxosulphate (VI) catalyst and dilute tetraoxosulphate (VI) acid
at about 750C to form either alkanol or alkanone. For example

H OH H O

[Type text]
 dil H 2 SO4
H C C H + H2O H C C H rearranged
H C C
Hg2 SO4
H
Ethyne Ethenol
H Ethanal

(f) Oxidation reaction of alkynes with KMnO4:

Alkynes decolourises acidified potassium tetraoxomangate(VII)
while it turns the alkaline solution green.

(g)Oxidation with ozone:

Alkynes react with ozone in the presence of some inert solvent such
as CCl4 to form ozonide.

CCl 4
H C C H + O3 H C C H
196−200 K
Ethyne
O O
ETHYNE
Physical properties of ethyne
1. Ethyne is a colourless gas with an ether-like odour when it is
absolutely pure. The impure ethyne has an unpleasant odour.
2. It is sparingly soluble in water.
3. It condensed into a liquid which boils at 83.6 0C,
4. It forms an explosive mixture with air
5. It is less than air.

Tests for ethyne

(a) With bromine water: when a little of bromine water is added to a
gas jar containing ethyne gas, the reddish brown colour of bromine
water disappear.
(b)With KMnO4: ethyne also decolourises acidified KMnO4 when it is
added to a gas jar containing the ethyne gas.
(c) With copper(I) and silver(I) ions: ethyne forms reddish brown and
white precipitate with an ammoniacal copper(I) chloride and
silvertrioxonitrate(V) respectively.

Uses of ethyne
1. It is used in oxyacetylene torch for welding metals.
2. It is also used as an illuminant in acetylene lamp used by the
hunters and miners.
3. It is a starting raw material for both the production of ethanoic
acid, ethanol and tetrachloromethane and also for the
preparation of plastics, synthetic rubber and synthetic firbres.
4. It is used in artificial ripening of fruits.
[Type text]
ALKANOL
Alcohols are the compounds containing hydroxyl group ( −OH ) attached to
the alkyl group. They are formed when one or more hydrogen atoms of an
alkane are replaced by one or more hydroxyl groups. Alkanols form an
homologous series having a general molecular formula CnH2n+1OH or simply
R-OH where R is a hydrocarbon radical attached to the functional group.
Examples are
H H H

H C O H H C C O H

H H H
Classification of alkanols
Alkanols are classified on the basis of:
i. The number of R groups in the molecule
ii. The number of – OH groups in the molecule

Classification based on the number of R groups in the molecule

Based on the number of R groups attached to the carbon with the hydroxyl
group in the molecule, alkanols are classified as:
i. Primary alkanols (10): These alkanols have one R group attached to
the carbon with the hydroxyl group. Eg Propan-1-ol.
H H H H

R C O H eg H C C C O H

H H H H

ii. Secondary alkanols (20): These alkanols have two R groups

attached to the carbon with the hydroxyl group. Eg Propan-2-ol.
H H OH H

R C R” eg H C C C H

H H H H

iii. Tertiary alkanols (30): These alkanols have three R groups attached
to the carbon with the hydroxyl group. Eg 2-methylpropan-2-ol.

H H OH H

R C R” eg H C C C H

R’’’ H H

H C H

H
[Type text]
Classification based on the number of –OH groups in the molecule
Based on the number of hydroxyl groups (-OH) in the molecule, alkanols are
classified as:
i. Monohydric alkanols: these are alkanols with one –OH group in their
molecules. E.g Ethanol CH3 CH2 OH
ii. Polyhydric alkanols: these are alkanols with more than one –OH
group in their molecules. They are named diols for two –OH groups,
triols for three –OH groups, tetraols for four –OH groups etc in their
molecules. E.g
- Ethan-1,2-diol (Ethylene glycol),
- Propan-1,2,3-triol (Glycerol),
- Hexan-1,2,3,4,5,6-hexaol (Sorbitol)

Preparation of alkanol
1. From Haloalkanes: When haloalkane is boiled with aqueous
potassium hydroxide, alkanol is produced.
C2H5Br(l) + KOH(aq) C2H5OH(l) + KBr(l)

2. By reduction of alkanals and alkanones: Alkanols are formed

when alkanals or alkanones are reduced by the addition of hydrogen in
the presence of nickel or platinum catalyst. The reduction can also be
carried out by treating alkanals and alkanones with reducing agents
such as sodium borohydride (LiAlH4).
Note
Aldehydes yield primary alkanols while ketones yield secondary
alkanol.

RCHO H2 RCH OH 2
Alkanal Primary alkanol

RCOR’ + H2 R CH R’
Alkanone

OH
Secondary alkanol

3. From carboxylic acids: In the presence of a strong reducing agent

(lithium aluminium hydride), carboxylic acids are reduced to primary
alkanols.
RCOOH + 4[H] LiAlH4 RCH2OH + H2O

4. From esters: Primary alkanols can also be obtained by reducing

esters using hydrogen in the presence of a catalyst.
RCOOR’ + 4[H] LiAlH4 RCH2OH + R’OH
Ester primary alkanols

5. From alkenes: alkenes undergo hydration (addition of water across

C=C bond) in the presence of dilute H2SO4 to produce alkanols.
6. By fermentation: ethanol can be prepared by fermentation process.
Fermentation is a slow chemical change produced in an organic
molecule by enzyme action of micro-organism such as yeast.

[Type text]
Oxidation of alkanols
i. Primary alkanols are oxidized to form alkanals. The alkanals are
further oxidized by the same oxidizing agent to give carboxylic
acids.

ii. Secondary alkanols are oxidized to alkanones in exactly the

same way primary alkanols are oxidized by the same oxidizing
agent to form alkanals. Unlike alkanals, the alkanones resist further
oxidation.

iii. Tertiary alkanols do not undergo oxidation. This is because

tertiary alkanols do not have any hydrogen on the –OH bearing
carbon and thus do not react with oxidizing agents.

Assignment:
Describe briefly with the aid chemical equations:
i. Combustion reaction of alkanol
ii. Reaction of alkanol with active metals
iii. Dehydration of alkanol
iv. Reaction with carboxylic acid

[Type text]
BENZENE
Benzene and its derivatives make up the aromatic hydrocarbons. In co
mposition, benzene is an unsaturated hydrocarbons with molecular formula
C6H6. The hydrocarbon derivatives of benzene are formed when one or more
atoms of benzene are replaced by hydrocarbons radicals.

CH3 C2H5

Benzene Methylbenzene Ethylbenzene

Sources of benzene
Benzene is obtained from the fractional distillation of coal tar. Coal tar is a
product of destructive distillation of coal along with ammoniacal liquor,
coal gas and coke. Further distillation of coal tar yields light oil which
contains benzene and its homologues. Certain quantities of benzene are
also produced in the catalytic cracking of petroleum.

Structure of benzene
The structure of benzene was proposed by Kekule in 1865. In this
structure, the six carbon atoms in benzene molecule form a closed chain
called benzene ring. Each carbon atom in the ring has a hydrogen atom
attached to it. The ring also contains double bonds in the alternate
positions. According to Kekule, the double bonds are not in fixed positions
but move between carbon atoms giving rise to alternate structures A and
B as shown below.

H H

H H H H

H H H H

H H

For convenient, the above structures can be simply represented by a regular

hexagon with the double bonds in the alternate positions.

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 Benzene

Resonance in benzene
Resonance is a phenomenon of representing a molecule with two or more
structures which have different arrangement of electrons but identical
arrangement of atoms.
The structures are called Canonical structures. The real structure of the
molecule is not represented by any one of the canonical structures. The
various canonical structures are usually separated by a double headed
arrow.

Benzene is one of the molecules that exhibit resonance. Resonance in

benzene is represented by the structures below:

A B C
The two structures A and B given by Kekule are the main contributing
structures. The hybrid structure is represented by inserting a circle in the
hexagon as shown in C above.

Laboratory preparation of benzene

Benzene is prepared in the laboratory by heating a mixture of sodium
benzoate and soda lime. Soda lime is a mixture of sodium hydroxide and
calcium oxide. The latter is added to the former to make it non-deliquescent.
COONa

+ NaOH + Na2CO3

Sodium benzoate Benzene

Physical properties of benzene

1. It is a colourless liquid with a characteristic aromatic smell
2. It is immiscible with water but miscible with organic solvents such as
ethanol, ether etc
3. It has a boiling point of 80.10C
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 4. Benzene solidifies when cooled into white crystalline mass, which
melts at 5.50C
5. Benzene has a relative density of 0.88

Chemical properties of benzene

Benzene undergoes the following reactions;
- Combustion
- Substitution
- Addition
1. Combustion reaction
When benzene is heated in air, it burns with sooty flame and produce
carbon(IV) oxide and water with evolution of large amount of energy.

2C6H6(l) + 15O2(g) 12CO2(l) + 6H2O(l)

2. Substitution reaction
This involves replacement of one or more hydrogen atoms of benzene
by other atoms or group of atoms. Substitution reactions of benzene
include;
- Halogenation
- Sulphonation
- Nitration

(a) Halogenation
In this reaction, a halogen (F, Cl, Br or I) replaces one hydrogen
atom of benzene. The reaction takes place in the presence of
metallic catalyst.
Cl

AlCl 3
+ Cl2 0 + HCl
37−47 C

Benzene Chlorobenzene

If excess attacking reagent is used, further substitution reaction may

take place in which other hydrogen atoms of benzene may also be
replaced. For example
Cl

Cl Cl

AlCl 3
+ 6Cl2 +
dark , cold
6HCl

Cl Cl
Benzene
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 Cl
Hexachlorobenzene
(b)Sulphonation
In this reaction, a sulphonic acid (–SO3H) group replaces a
hydrogen atom of benzene. This reaction is carried out by
replacing benzene with fuming tetraoxosulphate(VI) acid or
oleum (H2S2O7).
SO3H
2
+ H2SO4 + HCl

Benzene Benzene sulphonic acid

(c) Nitration
A nitro group (– NO2) replaces a hydrogen atom of benzene.
Nitration is carried out by heating benzene in a mixture of
concentrated trioxonitrate(V) acid and tetraoxosulphate(VI).

NO2

H 2 SO4
+ HO-NO2 0 + HCl
67 C

Benzene Nitrobenzene

(d)

3.

Br Br

2 Zn
R C C R
alcohol
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 Alkyne
Br Br

3.

 Sources
 General preparation
 Physical and chemical properties

Slaked lime = Ca(OH)2, the saturated solution of it is called Lime water

Caustic soda = NaOH
Sodalime = (a mixture of NaOH + CaO). Note CaO + H2O gives Ca(OH)2
Na2CO3 = Washing soda or soda ash
Quicklime = CaO

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