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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

Consider the following reaction sequence: Identify the structure of the major product Q .

Correct answer

2

Step-by-step solution

The reaction of cyclobutylmethanol with H₂SO₄ under heating is an acid-catalyzed dehydration. Protonation of the hydroxyl group and subsequent loss of a water molecule generates a primary cyclobutylmethyl carbocation. Due to the high angle strain in the four-membered ring, a 1,2-alkyl shift occurs, resulting in ring expansion to form a more stable secondary cyclopentyl carbocation (cyclobutylmethyl carbocation cyclopentyl carbocation). Loss of a proton from the cyclopentyl carbocation yields cyclopentene as the maj

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