Amine that cannot be prepared by Gabrielphthalimide synthesis is

Solution :
Only pure aliphatic $${1^ \circ }$$ amines can be prepared by Gabriel synthesis. Aromatic $${1^ \circ }$$ amines such as aniline, toluidines, etc., cannot be prepared by this method because aryl halides $$\left( {{C_6}{H_5}Cl\,\,{\text{or}}\,\,{C_6}{H_5}Br} \right)$$     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.