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JIPMER 2011
Exam
JIPMER
Year
2011
Subject
Chemistry
Chapter
Amines

JIPMER 2011 · Chemistry · Amines

Amine that cannot be prepared by Gabriel phthalimide synthesis is

Amine that cannot be prepared by Gabriel phthalimide synthesis isAmine that cannot be prepared by Gabriel phthalimide synthesis is

Options

  1. Aaniline
  2. Bbenzylamine
  3. Cmethylamine
  4. Diso-butylamine

Correct answer

A. aniline

Step-by-step solution

Only aliphatic primary amines can be prepared by Gabriel synthesis. Aniline cannot be prepared by this method because aryl halides (C6H5Cl\left(\mathrm{C}_6 \mathrm{H}_5 \mathrm{Cl}\right. or C6H5Br\mathrm{C}_6 \mathrm{H}_5 \mathrm{Br} ) do not undergo nucleophilic substitution with potassium phthalimide under ordinary conditions to give N -phenyl phthalimide (i.e., cleavage of C−X\mathrm{C}-\mathrm{X} bond in haloarenes is quite difficult). Amine that cannot be prepared by Gabriel phthalimide synthesis is
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