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MHT CET202526 Apr 2025Evening ShiftChemistryAlcohols Phenols and EthersActual

Identify the product ' A ' in the following reaction, Anisole [398 ~K ] HI A + Iodomethane

Options

  1. AAniline
  2. BIodobenzene
  3. CBenzenol
  4. DBenzene

Correct answer

C. Benzenol

Step-by-step solution

The cleavage of anisole with hydroiodic acid at 398 K proceeds through nucleophilic substitution on the alkyl carbon of this aryl alkyl ether system. The aryl-oxygen bond possesses partial double bond character due to resonance stabilization, rendering it resistant to cleavage. In contrast, the alkyl-oxygen bond is more labile. Protonation of the ether oxygen by HI yields an oxonium ion intermediate, which is then subject to S_N2 attack by the iodide nucleophile. This nucleophilic attack occurs exclusively at the m

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