Why can Gabriel Phthalimide synthesis prepare pure aliphatic amines but not aromatic amines (like Aniline)?
Expert Answer
It prepares pure aliphatic amines because the intermediate N-alkylphthalimide is formed via an reaction on an alkyl halide, avoiding over-alkylation. It fails for aromatic amines because aryl halides ( ) do not readily undergo nucleophilic substitution ( ) with the bulky phthalimide anion under typical conditions due to partial double bond character and electronic repulsion.