Amines

Question

Why cannot aromatic primary amines be prepared by Gabriel pthalimide synthesis?

Answer

Aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis because it 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  Gabriel pthalimide synthesis.

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