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JIPMER2011ChemistryAmines

Amine 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 ( C ₆ H ₅ Cl . or C ₆ H ₅ Br ) 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).

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