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JEE Chemistry 2023 Question with Solution

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

Four structural options are shown for the intermediate in cumene to phenol preparation, including acetophenone derivative, phenyl isopropyl ether, cumene, and cumene hydroperoxide structures labeled one to four.
  • A

    (1)

  • B

    (2)

  • C

    (3)

  • D

    (4)

Answer

Correct answer:C

Step-by-step solution

Standard Method

Given: The question asks for the intermediate formed in the cumene to phenol preparation in the presence of air.

Find: The correct intermediate among the given structures.

From the solution, the reaction scheme identifies the peroxide intermediate formed on oxidation of cumene by air.

Reaction scheme showing oxidation of cumene in air to cumene hydroperoxide, followed by acid cleavage to phenol and acetone, indicating the peroxide intermediate explicitly.

In the cumene process, cumene reacts with air to form cumene hydroperoxide as the key intermediate before cleavage to phenol.

Therefore, the structure corresponding to cumene hydroperoxide is the required intermediate.

The solution states Correct Option is C and Correct answer is (c). Hence, the correct option is C.

Common mistakes

  • Choosing cumene itself as the intermediate is incorrect because cumene is the starting material. The intermediate formed in air oxidation is cumene hydroperoxide.

  • Confusing oxidation with direct hydroxylation is incorrect. In the cumene process, phenol is not formed directly from cumene by a single substitution step; the reaction proceeds through a hydroperoxide intermediate.

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