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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4216

1-Cyclobutylethanol, (cyclobutyl attached to the carbinol carbon), is heated with conc. . After the carbocation rearrangements that relieve ring strain and give the most stable cation, the major alkene is:

  1. Avinylcyclobutane
  2. Bethylidenecyclobutane
  3. C1-methylcyclopentene
  4. D3-methylcyclopentene

Answer: C

The secondary cation next to the four-membered ring undergoes ring expansion (ring C-C bond shift), giving a cyclopentyl cation bearing a methyl group. A hydride shift gives the tertiary 1-methylcyclopentyl cation, and loss of a proton gives the most stable alkene, 1-methylcyclopentene.
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