Question:

Consider the following reaction}
Statement I:} In the above reaction, product formed will be a mixture of benzyl alcohol and iodobenzene.
Statement II:} In the above reaction, the \(-O-CH_2-\) bond is cleaved to give the product. Choose the correct answer.

Updated On: Apr 12, 2026
  • Both Statement I and Statement II are true
  • Both Statement I and Statement II are false
  • Statement I is true but Statement II is false
  • Statement I is false but Statement II is true
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The Correct Option is D

Solution and Explanation

Concept: Ethers react with HI via cleavage of the \(C-O\) bond. Aryl–O bonds are difficult to break due to resonance stabilization. Step 1: {Identify cleavage site} In the compound: \[ Ph-O-CH_2-Ph \] The bond between oxygen and benzyl carbon breaks because:
  • benzyl carbocation is stabilized
  • aryl–O bond is resistant to cleavage
Thus cleavage occurs at \[ -O-CH_2- \] Step 2: {Products formed} \[ Ph-O-CH_2-Ph + HI \] Products: \[ PhOH + PhCH_2I \] Thus products are phenol and benzyl iodide. Hence statement I (benzyl alcohol and iodobenzene) is incorrect. Statement II is correct.
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