Question

why aromatic primary amines cannot prepared by Gabriel phthalimide synthesis​

Answer 1

Answer:

Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines. ... But aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimide. Hence, aromatic primary amines cannot be prepared by this process.

Answer 2

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why aromatic primary amines cannot prepared by Gabriel phthalimide synthesis❓

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During Gabriel phthalimide synthesis, the reaction between phthalimide and ethanolic potassium hydroxide gives potassium salt of phthalimide.

The salt on heating with alkyl halide followed by alkaline hydrolysis gives corresponding primary amine.

Aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis as aryl halides do not undergo nucleophilic substitution with the salt formed by phthalimide.

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