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JEE Main levelSingle correct optionDifficulty 2 of 3g3225

The primary carbocation shown rearranges by a single 1,2-shift. Which structure shown is the most stable cation obtainable in this way?

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

Answer: D

The cation shown is the cyclopentylmethyl cation. A 1,2-hydride shift from the ring CH gives the 1-methylcyclopentyl cation, which is tertiary; ring expansion would give only the secondary cyclohexyl cation. The tertiary cation is more stable than the secondary one, so the 1-methylcyclopentyl cation is the most stable single-shift product.
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