Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product formed in the following reaction:
Correct answer
0
Step-by-step solution
The reactant is bicyclo[3.1.0]hex-2-en-4-ol. Treatment with concentrated H₂SO₄ and heat initiates dehydration. Protonation of the -OH group and subsequent loss of an H₂O molecule generates a carbocation at the C₄ position. This carbocation is adjacent to both a double bond (allylic) and a cyclopropane ring (cyclopropylcarbinyl). Driven by the relief of significant ring strain, the intermediate undergoes a ring expansion. The C₁-C₅ bond of the fused cyclopropane ring breaks, and its electrons shift to form a new bon