Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
When cyclobutylethene (vinylcyclobutane) is treated with dilute H ₂ SO ₄ , the major product formed is:
Options
- A2-Methylcyclopentan-1-ol
- B2-Cyclobutylethan-1-ol
- C1-Cyclobutylethan-1-ol
- 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