Amine that cannot be prepared by Gabriel phthalimide synthesis is

Question

Amine that cannot be prepared by Gabriel phthalimide synthesis is (A) aniline (B) benzylamine (C) methylamine (D) iso-butylamine

Tardigrade Admin · Accepted Answer

Aniline cannot be prepared by this method because aryl halides do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions to give N-phenyl phthalimide (i.e., cleavage of C-X bond in haloarenes is quite difficult). <img class="img-fluid question-image" alt="image" src="https://cdn.tardigrade.in/img/question/chemistry/d44fbe4d0d48e108af6d864a2e7ae0e8-.png" />

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

aniline

benzylamine

methylamine

iso-butylamine

Aniline cannot be prepared by this method because aryl halides do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions to give $N$ -phenyl phthalimide (i.e., cleavage of $C - X$ bond in haloarenes is quite difficult).

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

aniline

benzylamine

methylamine

iso-butylamine

Aniline cannot be prepared by this method because aryl halides do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions to give N-phenyl phthalimide (i.e., cleavage of C−X bond in haloarenes is quite difficult).

Aniline cannot be prepared by this method because aryl halides do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions to give $N$ -phenyl phthalimide (i.e., cleavage of $C - X$ bond in haloarenes is quite difficult).