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JEE Main levelSingle correct optionDifficulty 2 of 3nc007

Which of the following amines cannot be prepared by the Gabriel phthalimide synthesis?

  1. A
  2. B
  3. C
  4. D

Answer: B

The Gabriel synthesis needs an attack of phthalimide anion on an alkyl halide. Ethyl bromide, benzyl chloride and propyl bromide are suitable halides. Bromobenzene or chlorobenzene does not undergo this substitution because the bond is strengthened by partial double bond character and the ring blocks backside attack, so aniline cannot be made.
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