Introduction to Substitution Reactions

Substitution reactions are a fundamental concept in organic chemistry. A substitution reaction is

one in which one group atom attached to the carbon atom in a molecule is displaced by
another. In this reaction, the incoming group becomes attached to the carbon atom from which
the leaving group departs.

Types of Substitution Reactions

Depending on the nature of the substituent, generally there are two types of substitution reaction

1. Electrophilic substitution reaction

2. nucleophilic substitution reaction

. Electrophilic Substitution

Involves the replacement of an atom or group of atoms by an electrophile. This reaction

generally occur in aromatic ring by an electrophile.

The reaction occur in two steps:

a. Generation of sigma complex

The sigma complex is formed when the electrophile reacts with the aromatic compound, creating
a temporary bond between the carbon and electrophile. This complex is highly unstable.

b. Elimination of proton

The second step involves the elimination of a proton from the sigma complex, resulting in the
formation of the final substitution product.

. Nucleophilic Substitution

The nucleophilic substitution reaction occurs when a nucleophile reacts with an

electrophilic center, replacing an atom or group of atoms. This type of reaction is commonly
denoted as SN. There are various types of nucleophilic substitution reactions, including SN1
and SN2, which differ in terms of their reaction mechanisms and reaction rates.

SN1

In an SN1 reaction, the nucleophilic substitution occurs through a two-step process. In the first
step, the leaving group detaches from the substrate, forming a carbocation intermediate. This
carbocation is highly reactive and can be attacked by a nucleophile in the second step, leading to
the formation of the substitution product.

SN2

In contrast, SN2 reactions proceed through a single-step mechanism where the nucleophile
directly displaces the leaving group in an inversion of stereochemistry. The stereochemistry
inversion is due to the nucleophile's attack on the opposite side of the substrate's leaving group.

3. Free Radical Substitution

Energy Profile Diagram