Question

Account for the following:
Gabriel phthalimide synthesis is not preferred for preparing aromatic primary amines.

Answer 1

Gabriel phthalimide synthesis not prefered for preparing aromatic primary amines because amine formation involves nucleophilic substituion 2 ( ) SN 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. As nucleophilic substitution reactions are very difficult in aryl halides.