Question

Why gabriel phthalimide synthesis is not preferred for the preparation of primary aromatic amine?

Answer 1

Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines. It involves nucleophilic substitution (SN2) of alkyl halides by the anion formed by the phthalimide.

But aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimide.

Hence, aromatic primary amines cannot be prepared by this process.

Answer 2

$\huge\textcolor{indigo}{\rm{Answer :-}}$

Aromatic primary amines can not be prepared by Gabriel Phthalimide synthesis, because aryl halides do not undergo nucleophillic substitution reaction with the anion formed by the phthalamide.