question_answer

Amine that cannot be prepared by Gabriel phthalimide synthesis is

A)  aniline                                 

B)  benzylamine

C)  methylamine    

D)         iso-butylamine

E)  tertiary butylamine

Correct Answer: A

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)