Question
Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis ?

Answer

Aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis because in aryl halide double bond character is attained in carbon halogen bond due to resonance ( + M effect) so bond becomes strong due to which aryl halide do not undergo nucleophilic substitution with the anion formed by phthalimide.

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