Question
Why cannot aromatic primary amines be prepared by Gabriel pthalimide synthesis?
Solution
Aromatic primary amines cannot be prepared by Gabriel phthalimide synthesis because it used for the preparation of aliphatic primary amines. It involves nucleophilic substitution (SN2) of alkyl halides by the anion formed by the phthalimide. But aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimide.
Hence, aromatic primary amines cannot be prepared by Gabriel pthalimide synthesis.
Hence, aromatic primary amines cannot be prepared by Gabriel pthalimide synthesis.
