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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

When cyclobutylethene (vinylcyclobutane) is treated with dilute H ₂ SO ₄ , the major product formed is:

Options

  1. A2-Methylcyclopentan-1-ol
  2. B2-Cyclobutylethan-1-ol
  3. C1-Cyclobutylethan-1-ol
  4. D1-Methylcyclopentan-1-ol

Correct answer

D. 1-Methylcyclopentan-1-ol

Step-by-step solution

Protonation of the double bond in cyclobutylethene (vinylcyclobutane) by dilute H ₂ SO ₄ follows Markovnikov's rule, yielding the more stable secondary carbocation, the 1-cyclobutylethyl cation. To relieve the significant ring strain of the four-membered cyclobutane ring, a ring expansion occurs. A C - C bond from the ring migrates to the adjacent carbocation center, expanding the ring to a five-membered cyclopentane ring. This forms the 2-methylcyclopentyl cation, which is still a secondary carbocation. To achieve

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