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JEE Main levelSingle correct optionDifficulty 2 of 3o2238

The alkene shown reacts with (no peroxide). Which structure is the major product?

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

Answer: C

The alkene is (prop-1-en-2-yl)cyclopentane. Protonation of the terminal carbon gives a tertiary carbocation directly. A ring expansion would convert it into a secondary cyclohexyl cation, which is less stable, and the cyclopentane ring has little angle strain to relieve, so no rearrangement occurs. Bromide captures the tertiary cation to give (2-bromopropan-2-yl)cyclopentane, Structure C.
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