Answer:
Aromatic primary amines, i.e.,
aniline cannot be prepared by Gabriel phthalimide reaction. The reason being
that preparation of aniline by Gabriel-phthalimide reaction requires the
treatment of pot. phthalimide with \[{{C}_{6}}{{H}_{5}}Cl\]or \[{{C}_{6}}{{H}_{5}}Br\].
Since aryl halides do not undergo nucleophilic substitution under ordinary laboratory
conditions, therefore, \[{{C}_{6}}{{H}_{5}}Cl\] or \[{{C}_{6}}{{H}_{5}}Br\]
does not react with pot. phthalimide to give N-phenyl phthalimide and hence
aniline cannot be prepared by this method.
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