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Question

Amine that cannot be prepared by Gabriel phthalimide synthesis is:

A
aniline
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B
benzylamine
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C
methylamine
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D
iso-butylamine
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Solution

The correct option is A aniline
The Gabriel phthalimide synthesis is a chemical reaction that transforms primary alkyl halides into primary aliphatic amines.
Aniline can't be prepared by this method because aryl halide do not undergo nucleophilic substitution reaction with Potassium phthalimide under ordinary condition to give N-phenyl phthalimide as cleavage of CX bond in haloarene in difficult. Hence correct option is (a).
Except (a) all other are primary amine and can be prepared easily using this method.

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