Question

Amine that cannot be prepared by Gabrielphthalimide synthesis is

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

Answer 1

Answer: (A)

Only pure $1^{°}$ 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 (i.e., cleavage of $C—X$ bond in haloarene is quite difficult) with potassium phthalimide under ordinary conditions to give $N$-phenyl phthalimide.