Why cannot aniline be prepared by Gabriel phthalimide synthesis? - Vidyadip

Question

Why cannot aniline be prepared by Gabriel phthalimide synthesis?

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Answer

Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines.
It involves the nucleophilic substitution 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, aniline cannot be prepared by Gabriel phthalimide synthesis.

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