JEE Main · 2020 · 08 Jan 2020 · Shift 2 · Alcohols Phenols and Ethers

The major product in the following reaction is

(A)(see structure)
✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)

Answer: (A)

Solution

Meta-chloroperbenzoic acid converts the double bond into an epoxide. Warm aqueous acid then protonates the epoxide oxygen and opens the ring; because the protonated epoxide carries most of its positive charge on the more substituted carbon, water attacks there, and the two oxygen functions end up on adjacent carbons in a trans arrangement. The major product is therefore the trans alcohol with the new

- OH

at the more substituted position.

JEE Main · 2020 · 08 Jan 2020 · Shift 2 · Single correct option

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