Question

Amine that cannot be prepared by Gabriel- phthalimide synthesis is

• A. aniline
• B. benzyl amine
• C. methyl amine
• D. iso-butyl amine

Answer 1

Answer: (A)

aniline

Answer 2

Only aliphatic primary amines can be prepared by Gabriel synthesis. Aniline cannot be prepared by this method because aryl halides ( ${{C}_{6}}{{H}_{5}}Cl$ or ${{C}_{6}}{{H}_{5}}Br$ ) do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions to give N-phenyl phthalimide (ie, cleavage of $CX$ bond in haloarenes is quite difficult)
( $RX=$ aliphatic halide)