Question

Acetanilide on nitration followed by alkaline hydrolysis mainly gives –
(a) o-Nitroaniline
(b) p-Nitroaniline
(c) m-Nitroaniline
(d) 2, 4, 6-Trinitroaniline

Answer 1

answer is o-nitroaniline

Answer 2

Answer: The correct answer is b) p-nitroaniline.

Explanation:

Acetanilide on nitration followed by alkaline hydrolysis :

It occurs under the presence of H2SO4 and HNO3

It gives both o nitroaniline and p nitroaniline.

But the major product is p nitroaniline.

This is electrophilic substitution reaction.

The acetamido group is bulky and thus it causes steric hindrance.

So the p product is major product.

The N is changed as lone pair is transferred through cross conjugation.