The products formed in the reaction of cumene with $\mathrm{O}_{2}$ followed by treatment with dil. HCl are:

(B) (see structure) and $\mathrm{CH}_{3}-\mathrm{OH}$

JEE Main · 2019 · 09 Jan 2019 · Shift 2 · Alcohols Phenols and Ethers

The products formed in the reaction of cumene with

O_{2}

followed by treatment with dil. HCl are:

(A)(see structures)
A
B
(B)(see structure) and $CH_{3} - OH$
(C)(see structures)
A
B
✓ Correct
(D)(see structures)
A
B

Answer: (C)

Solution

Cumene, which is isopropylbenzene, is the industrial route to phenol. Air oxidation puts an

- OOH

group on the benzylic carbon to give cumene hydroperoxide,

C X_{6} H X_{5} C (CH X_{3}) X_{2} OOH

. Warming this with dilute acid drives a hydroperoxide rearrangement in which the phenyl group migrates to oxygen, and hydrolysis then splits the intermediate into two products: phenol,

C X_{6} H X_{5} OH

, together with acetone,

(CH X_{3}) X_{2} CO

JEE Main · 2019 · 09 Jan 2019 · Shift 2 · Single correct option

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