Consider the following list of amines: Ethylamine, Aniline, Benzylamine, tert-Butylamine, N-Methylaniline, p-Toluidine. How many of the above amines can be successfully prepared using the Gabriel phthalimide synthesis?

Step-by-step solution

Gabriel phthalimide synthesis involves the nucleophilic substitution ( S_ N 2 ) of an alkyl halide by the phthalimide anion, followed by hydrolysis. It is strictly limited to the preparation of unhindered primary aliphatic or aralkyl amines. 1. Ethylamine: It is a primary aliphatic amine. Its corresponding halide (ethyl halide) easily undergoes S_ N 2 . It can be prepared. 2. Aniline: It is an aromatic amine. Aryl halides do not undergo nucleophilic substitution with the phthalimide anion. It cannot be prepared. 3.