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JEE Main levelSingle correct optionDifficulty 2 of 3nc242

The amine shown is to be prepared by the Gabriel synthesis (potassium phthalimide, then hydrazine). Which halide should be used?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

The target shown is 3-methylbutan-1-amine (isopentylamine). The Gabriel route installs the nitrogen on the carbon carrying the halogen without changing the carbon skeleton, so the halide must have the same skeleton: 1-bromo-3-methylbutane. The other halides have different carbon skeletons.
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