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| 1. |
Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis? |
Answer» Solution :The key step in the Gabriel phthalimide SYNTHESIS is a `S_(N)2` REACTION in which the nucleophile, phthalimide anion displaces the halide ion from alkyl halide to form N-alkylphthalimide. This upon subsequent acid or alkaline hydrolysis GIVES the corresponding aliphatic primary amine.   Since aryl halides do not undergo nucleophilic substitution reactions easily, therefore, arylamines, i.e., aromatic primary amines cannot be prepared by Gabriel phthalimide reactions. |
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