The major product obtained in the following reaction is:
(A)(see structure)
(B)(see structure)✓ Correct
(C)(see structure)
(D)(see structure)
Answer: (B)
Solution
This is an acid-catalysed rearrangement. The alcohol is first protonated and loses water to give a carbocation, which is strained in its original ring. A Wagner-Meerwein shift then migrates a bond so the positive charge moves onto a more stable, larger six-membered ring. Loss of a proton followed by keto-enol tautomerism finishes the sequence, delivering the six-membered ring ketone as the major product.
JEE Main · 2019 · 08 Apr 2019 · Shift 2 · Single correct option
