Question

What is the order of quantities of all isomers of nitroaniline formed on the reaction of aniline with nitric acid and sulphuric acid at 288K?

(a) ortho > meta > para

(b) para > ortho > meta

(c) para > meta > ortho

(d) meta > para > ortho

This question was posed to me by my college director while I was bunking the class.

This key question is from Amines Chemical Reactions in portion Amines of Chemistry – Class 12

Answer 1

The correct option is (c) para > meta > ortho

For explanation: Nitration of aniline produces nitro derivatives. Under controlled conditions, aniline is protonated (by strong acidic medium) to form anilinium ion, which is meta directing. Therefore, apart from p-nitroaniline (51%) and o-nitroaniline (2%), a significant amount of m-nitroaniline (47%) is also formed.