AX+AY+XY

CH3Br aqueous OH CH3OH + Br

A X + Y A Y+X

Different types of organic iii) Free radical substitution

reactions Nucelophilic substituion:
Organic compounds undergo This reaction can be
many number of reactions, represented as
however in actual sense we can + + + NO2 + H NO2
fit all those reactions into the Here Y– is the incoming
below mentioned six categories. nucleophile or and attacking
Substitution reactions species and x– is the leaving
group.
Addition reactions
Example: Hydrolysis of alkyl
Elimination reactions
halides
Oxidation and reduction
A X + Y A Y+X
reactions
Aliphatic nucleophilic
Rearrangement reactions substitution reactions take
Combination of the above places either by SN1 or SN2
mechanism. Detailed study of
12.2.1 Substitution reaction the mechanisms is given in unit
(Displacement reaction) 14.
In this reaction an atom or a Electrophilic Substitution
group of atoms attached to a CH4 + Cl CH3+HCl
carbon atom is replaced by a
Here Y+ is an electrophile
new atom or a group of atoms.
Based on the nature of the Example: Nitration of Benzene
attacking reagent, this reactions R- X + E R - E + X
can be classified as Mechanism of aromatic
i) Nucleophilic substitution electrophilic substitution
ii) Electophilic substitution reactions (EAS) is discussed in
detail in unit 13.
Free radical substitution

+
Aliphatic electrophilic
substitution
A general aliphatic electrophilic
substitution is represented as

R2NH + NO → R2N–NO + H
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H H I H H H H - I H H H OH H H H W Y A B W Y H2C CH2 + Br H Br
H H - OH H2SO4 A B + Y A B + W 2C CH2 + Br Br H2C CH2 Br Br

12.2.2 Addition reactions Brominatin of alkene to give

bromo alkane is an example for
It is a characteristic reaction of
this reaction.
an unsaturated compound
(compounds containing C-C
localised double or triple bond). Acetaldehyde
In this reaction two molecules
Nucleophilic addition reaction
combine to give a single
product. Like substitution this
reaction also can be classified Acetaldehyde cyanohydrin
as nucleophilic, electrophilic
Example: addition of HCN to
and freeradical addition
acetaldehyde
reactions depending the type of
A B + Y A B + W W Y A B+ W Y A
reagent which initiates the
BY W
reaction. During the addition
reaction the hydridisation of the Free radical addition Reaction:
substrate changes (from sp2 →
A General freeradical addition
sp3 in the addition reaction of
reaction can be represented as
alkenes or sp → sp2 in the
below.
addition reaction of alkynes) as
only one bond breaks and two www.tntextbooks.in 173
new bonds are formed.
AB+YAB+WWYABWY
Electrophilic Addition reaction
A general electrophilic addition
reaction can be represented as
below.
H3C CH + H H3C CH OH CN OH
O CN
H2C CH2 + CH3 CH2 Br H Br
Benzoyl Peroxide
In the above reaction, Benzoyl peroxide acts as a
radical initiator. The mechanism involves free
radicals.

Elimination reactions:

In this reaction two substituents are eliminated

from the molecule, and a new C-C double bond is
formed between the carbon atoms to which the
eliminated atoms/groups are previously attached.
Elimination reaction is always accompanied with
change in hybridisation.

Example: n-Propyl bromide on reaction with

alcoholic KOH gives propene. In this reaction
hydrogen and Br are eliminated.