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Aniline can not be prepared by Gabriel phthalimide synthesis due to-

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Gabriel phthalimide synthesis is used for the prepartion of aliphatic primary amines. It involves nucleophilic substitution `(S_(N)2)` of alkyl halides by the anion formed by the phtalimide.
image
But aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimed.
image
Hence, aromatic primary amines cannot be preparted by this process.

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