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JEE Main levelSingle correct optionDifficulty 2 of 3g3228

The secondary carbocation shown rearranges by a single 1,2-shift to the most stabilised cation reachable by one shift. Which structure shown is that cation?

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

Answer: D

The cation shown is the 2-methylcyclohexyl cation. A 1,2-hydride shift from the adjacent ring carbon bearing the methyl group moves the charge to that carbon. This gives the 1-methylcyclohexyl cation, which is tertiary and therefore more stable than the secondary cation; the other structures are not formed by a single stabilising shift.
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