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