Gabriel synthesis involves treating phthalimide with ethanolic potassium hydroxide, followed by heating with alkyl halide and alkaline hydrolysis to produce primary amines. However, this method cannot be used for aromatic primary amines as aryl halides do not undergo nucleophilic substitution with the phthalimide anion.
Explain the Gabriel phthalimide synthesis method for preparing primary amines and its limitation with aromatic amines.
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Gabriel phthalimide synthesis involves the reaction of phthalimide with an alkyl halide to form N-alkyl phthalimide, which is then treated with hydrazine to produce the primary amine. This method is useful for preparing primary amines from alkyl halides, providing a practical alternative to other amine synthesis methods. However, it is limited in the case of aromatic amines, as the reaction with hydrazine is sluggish and often yields unsatisfactory results. Aromatic amines may undergo side reactions, making Gabriel synthesis less efficient for this class of compounds.