Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the major product formed in the following reaction:
Correct answer
0
Step-by-step solution
The given reactant is benzene oxide (7-oxabicyclo[4.1.0]hepta-2,4-diene), which contains a single oxygen atom. In the presence of concentrated H ₂ SO ₄ , the epoxide undergoes an acid-catalyzed rearrangement. The mechanism proceeds as follows: 1. The oxygen atom of the epoxide is protonated by the acid. 2. The epoxide ring opens to form a resonance-stabilized carbocation (a cyclohexadienyl cation). 3. A 1,2-hydride shift (NIH shift) occurs, leading to the formation of a protonated cyclohexadienone intermediate. 4.