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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc181

Which of the following amines can be prepared from a suitable alkyl halide by the Gabriel phthalimide synthesis (potassium phthalimide, then hydrolysis or hydrazinolysis)?

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

Answer: A, B

The method works for primary alkyl halides (SN2): propyl halide gives propylamine and benzyl halide gives benzylamine. Aniline would need an aryl halide, which does not react. The tert-butyl halide undergoes elimination instead of SN2, so tert-butylamine is not obtained.
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