Question:

Which of the following compounds can be prepared in good yield by Gabriel phthalimide synthesis?

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Gabriel synthesis gives only primary aliphatic amines (via SN2 on an alkyl halide); aryl halides do not react.
Updated On: Nov 5, 2026
  • \(\mathrm{CH_3-CH_2-NHCH_3}\)
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The Correct Option is B

Solution and Explanation

Gabriel phthalimide synthesis: potassium phthalimide + alkyl halide (SN2) followed by hydrolysis gives a primary aliphatic amine \(\mathrm{R-NH_2}\).
Option (1) aniline: needs an aryl halide, which does not undergo SN2 with the phthalimide anion, so it cannot be made.
Option (2) benzylamine \(\mathrm{C_6H_5CH_2NH_2}\): from benzyl chloride, a primary alkyl halide, so it can be made in good yield.
Option (3) phenylacetamide is an amide, not an amine.
Option (4) \(\mathrm{CH_3CH_2NHCH_3}\) is a secondary amine and is not obtained.
Answer: (2) benzylamine
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