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JEE Main levelSingle correct optionDifficulty 2 of 3g3224

The primary carbocation shown undergoes ring expansion by a 1,2-alkyl shift (a ring C-C bond migrates to the cationic carbon). Which structure shown is the cation formed?

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

Answer: D

The cation shown is the cyclobutylmethyl cation. Migration of a ring C-C bond to the CH carbon enlarges the four-membered ring to a five-membered ring and leaves the charge on a ring carbon. The product is the cyclopentyl cation, which is secondary rather than primary and also relieves the ring strain of cyclobutane.
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