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Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis ? |
Answer» Solution :In GABRIEL phthalimide synthesis, `S_(N)2` REACTION takes place 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.  Due to resonance in Ar-X, there is some double bond character because of which, it is difficult to break Ar - X bond. THEREFORE, aryl halides do not underog nucleophilic substitution reactions easily. Thus, aromatic primary amines cannot be prepared by Gabriel phthalimide reaction. |
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