Chapter 22, Problem 22.22P

Interpretation Introduction

Interpretation:

The synthesis of deuterobenzene from aniline is to be proposed.

Concept introduction:

The Sandmeyer reaction is the aromatic substitution reaction of an aromatic amino group from the preparation of its diazonium salt using copper salts as the catalyst. It is a very important transformation of organic reactions because some substituents are not directly incorporated on the aromatic ring. Deuterobenzene is produced when aniline is treated with sodium nitrate under acidic condition, followed by copper salts. This is not a simple electrophilic aromatic substitution reaction. Overall, the amino group is replaced by D in a multistep mechanism. First aniline is converted into diazotization, which is then producing the benzenediazonium ion, which can be converted into the target molecule.