Q72 / 160 · JIPMER 2011 · Chemistry

Amine that cannot be prepared by Gabriel phthalimide synthesis is

  • Correct answer
    A
    aniline
  • B
    benzylamine
  • C
    methylamine
  • D
    iso-butylamine

Solution

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

Hence, the correct answer is option: 'A'.

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