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  4. Amine that cannot be prepared by Gabriel- phthalimide synthesis is

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Q. Amine that cannot be prepared by Gabriel- phthalimide synthesis is

KEAMKEAM 2010Amines

Solution:

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)

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