Question

How many electrophilic aromatic substitution products are obtained from chlorination of

1. o-xylene?
2. p-xylene?
3. m-xylene?

Short answer

a.

b.

c.

Step-by-step solution

Step-by-Step SolutionStep 1: Electrophilic aromatic substitution

Electrophilic aromatic substitution is the substitution of one group in place of the group already attached to the aromatic ring.The products are formed in major and minor quantities depending upon the steric hindrance.

The product obtained from chlorination of o-xylene

(a) When o-xylene undergoes chlorination in the presence of ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$, two products are formed. The product present on the right side is formed in a lesser amount because of steric hindrance. Thus, the product obtained is,

Chlorination of o-xylene

The product obtained from chlorination of p-xylene

(b) When p-xylene undergoes chlorination in the presence of ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$, only one product is formed. The four positions are equivalent so that Cl can be bonded at any place. Thus, the product obtained is,

Chlorination of p-xylene

The product obtained from chlorination of m-xylene

(c) When m-xylene undergoes chlorination in the presence of ${\text{Cl}}_{\text{2}}{\text{/FeCl}}_{\text{3}}$, two products are formed. The two products are in major and minor form. The minor product is formed because of steric hindrance. Thus, the product obtained is,

Chlorination of m-xylene