Questions/Amines/Why can Gabriel Phth...
Preparation of AminesAmines

Why can Gabriel Phthalimide synthesis prepare pure 11^\circ aliphatic amines but not 11^\circ aromatic amines (like Aniline)?

Expert Answer

It prepares pure 11^\circ aliphatic amines because the intermediate N-alkylphthalimide is formed via an SN2S_N2 reaction on an alkyl halide, avoiding over-alkylation. It fails for aromatic amines because aryl halides ( ArXAr-X ) do not readily undergo nucleophilic substitution ( SN2S_N2 ) with the bulky phthalimide anion under typical conditions due to partial double bond character and electronic repulsion.

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