JEE Main · 2023 · 25 Jan 2023 · Shift 1 · Alcohols Phenols and Ethers

In the cumene to phenol preparation in presence of air, the intermediate is

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

Answer: (D)

Solution

In the preparation of phenol from cumene, isopropylbenzene is first oxidised by atmospheric oxygen at its benzylic carbon, where the tertiary hydrogen is readily removed. This installs an

- O - O - H

group on the carbon joining the ring to the two methyls, giving cumene hydroperoxide, which acid then cleaves into phenol and acetone. The intermediate formed in the air-oxidation stage is cumene hydroperoxide.

JEE Main · 2023 · 25 Jan 2023 · Shift 1 · Single correct option

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