Question

Aromatic primary amines cannot be prepared by Gabriel Phthalimide synthesis. 

Hint:

Aromatic rings are less reactive in nucleophilic substitution reactions due to the resonance stabilization of the ring.

Answer 1

The Gabriel Phthalimide synthesis, which converts phthalimide and an alkyl halide into an amine, is effective for aliphatic amines but not for aromatic primary amines. Aryl halides are less reactive in this process due to the resonance stabilization of aromatic rings, which impedes nucleophilic attack by the amide ion. Consequently, Gabriel's synthesis is inefficient for producing aromatic primary amines.