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COMEDK20269 May 2026Evening ShiftChemistryAlcohols Phenols and EthersActual

A compound [X] undergoes reactions as given. Identify compounds [C] and [D] formed in these reactions.

Options

  1. A[C]: Benzoic acid [D]: Iodoform
  2. B[C]: Benzene [D]: 2-iodo-propane
  3. C[C]: Benzoquinone [D]: Iodoform
  4. D[C]: 4–Iodophenol [D]: 1-iodo-propane

Correct answer

C. [C]: Benzoquinone [D]: Iodoform

Step-by-step solution

The given starting compound is isopropyl phenyl ether, Ph-O-CH(CH₃)₂ . Reaction with concentrated HI leads to the cleavage of the ether. Due to the partial double bond character of the O-phenyl bond (arising from resonance), the cleavage occurs at the O-isopropyl bond. This yields phenol and isopropyl iodide. Ph-O-CH(CH₃)₂ + HI PhOH + CH₃-CH(I)-CH₃ Since [A] is the aromatic product, [A] is Phenol and [B] is Isopropyl iodide. Phenol [A] undergoes oxidation with acidified dichromate ( Cr₂O₇²⁻ / H^+ ) to form p-benzoq

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