Asked in Premeth Test 22 — Carboxylic Acids, Alcohols and Phenols (24 March 2025) 2025Moderate

Name the compound which forms phenol when oxidized by atmospheric oxygen in the presence of a metal catalyst:

Correct answer: A. Cumene

  • A. Cumene
  • B. Toluene
  • C. Benzene
  • D. Aniline

Explanation

The compound that forms phenol when oxidized by atmospheric oxygen in the presence of a metal catalyst is cumene (isopropylbenzene). This process is known as the Hock process or the cumene process, and it's the primary industrial method for producing phenol and acetone.Here's a simplified overview of the reaction:Oxidation of Cumene: Cumene is oxidized by air (oxygen) in the presence of a radical initiator to form cumene hydroperoxide. Acid-Catalyzed Cleavage: The cumene hydroperoxide is then treated with dilute acid (usually sulfuric acid), which causes it to cleave, producing phenol and acetone. The reaction is as follows:C₆H₅CH(CH₃)₂ (Cumene) + O₂ → C₆H₅C(CH₃)₂OOH (Cumene hydroperoxide)C₆H₅C(CH₃)₂OOH --(H⁺)--> C₆H₅OH (Phenol) + CH₃COCH₃ (Acetone)

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About Phenols

Phenols contain a hydroxyl group directly bonded to an aromatic ring, making them more acidic than alcohols because the phenoxide ion is resonance-stabilised. Reactions include ionisation with bases, electrophilic substitution, bromination, nitration and oxidation, with attention to the difference between phenols and aliphatic alcohols.

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