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JEE Main levelSingle correct optionDifficulty 2 of 3o4253

The alcohol shown is heated with concentrated acid. The secondary carbocation expands the four-membered ring to a more stable cation. Which structure is the major alkene?

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

Answer: D

The alcohol is 1-cyclobutylethanol. Ionisation gives a secondary cation next to a strained cyclobutane, and a ring-expansion alkyl shift gives the tertiary 1-methylcyclopentyl cation, relieving angle strain. Loss of a ring hydrogen then gives the Saytzeff product 1-methylcyclopentene, not the unrearranged vinylcyclobutane.
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