NCERT · Class 12 · Chemistry · AminesWhy cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?

Aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis because aryl halides do not undergo nucleophilic substitution with the potassium phthalimide anion under ordinary laboratory conditions. The carbon-halogen bond in aryl halides possesses a partial double bond character due to resonance stabilization and resonance effects involving the lone pairs on the halogen atom and the aromatic ring pi system, making the halide extremely unreactive toward nucleophilic displacement reactions.