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13.12 Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?
Answers (1)
Gabriel phthalimide synthesis is used for mainly aliphatic primary amine preparation. Phthalimide reacts with ethanolic potassium hydroxide and produces potassium salt of phthalimide which on heating with alkyl halide followed by alkaline hydrolysis gives corresponding primary amine.
Aromatic amines cannot be produced by this method due to the inability of aryl halides to do nucleophilic substitution reaction with anion produced by phthalimide.
Hence aromatic amines cannot be produced by this method.
{if R = Aromatic compound}
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