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Question 54

The products formed in the reaction of cumene with $$O_2$$ followed by treatment with dil HCl are:

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  1. Step 1: Radical Oxidation to Cumene Hydroperoxide

    When cumene is reacted with oxygen ($$\text{O}_2$$) in the presence of air, a free-radical oxidation process occurs selectively at the highly reactive tertiary benzylic carbon atom. This leads to the formation of cumene hydroperoxide as a stable intermediate:

    $$\text{C}_6\text{H}_5\text{--CH(CH}_3)_2 + \text{O}_2 \rightarrow \text{C}_6\text{H}_5\text{--C(CH}_3)_2\text{--O--O--H}$$

  2. Step 2: Acid-Catalyzed Cleavage (Hock Rearrangement)

    Subsequent treatment of cumene hydroperoxide with dilute hydrochloric acid ($$\text{dil. HCl}$$ or $$\text{H}^\oplus$$) protonates the terminal oxygen atom. This triggers a simultaneous 1,2-phenyl migration to the electron-deficient oxygen atom with the loss of a water molecule.

    The resulting oxacarbocation intermediate is then attacked by water, undergoing proton transfer and bond cleavage to yield two highly valuable chemical industrial products: Phenol and Acetone (propan-2-one).

    $$\text{C}_6\text{H}_5\text{--C(CH}_3)_2\text{--O--O--H} \xrightarrow{\text{H}^\oplus, \, \text{H}_2\text{O}} \text{C}_6\text{H}_5\text{OH} + \text{CH}_3\text{--CO--CH}_3$$

Conclusion:

The industrial preparation of phenol from cumene cleanly delivers phenol as the principal product along with acetone as a commercially significant co-product.

Answer: Option C — Phenol and Acetone

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