Chapter 23, Problem 23.32P

Interpretation Introduction

Interpretation:

The synthesis of an aniline derivative from benzene is to be shown.

Concept introduction:

The aromaticity of the benzene ring disappears during electrophilic addition reactions. Electrophilic aromatic substitution reactions grant permission to incorporate lots of substituents onto an aromatic ring, however, most of the substituents cannot be put in place directly to the aromatic ring. Nitration of benzene is carried out with nitric acid and sulfuric acid, which yields nitrobenzene. The reduction of nitrobenzene yields aniline. The reactivity of a substituent attached to the ring is to be temporarily surpassed and block a particular site of the ring. The amino group is a good Lewis base and the lone pairs on nitrogen available to form a bond to a Lewis acid. This is a strongly deactivating group, making the Friedel-Craft reaction unfeasible.