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The major products formed by heating C6H5CH2-O-C6H5 with HI are

  • A.\(\mathrm{C_{6}H_{5}CH_{2}I}\) and \(\mathrm{C_{6}H_{5}\text{-}CH_{2}OH}\)
  • B.\(\mathrm{C_{6}H_{5}CH_{3}}\) and \(\mathrm{C_{6}H_{5}OH}\)
  • C.\(\mathrm{C_{6}H_{5}CH_{2}I}\) and \(\mathrm{C_{6}H_{6}}\)
  • D.\(\mathrm{C_{6}H_{5}\text{-}CH_{2}OH}\) and \(\mathrm{C_{6}H_{5}I}\)
  • E.\(\mathrm{C_{6}H_{5}CH_{2}I}\) and \(\mathrm{C_{6}H_{5}OH}\)

Answer: E

The products are C6H5CH2I and C6H5OH.

HI cleaves ethers by protonating the oxygen and then letting iodide attack a carbon. The O-phenyl bond has partial double bond character (the oxygen's lone pair is delocalised into the ring), and iodide cannot attack an sp2 ring carbon, so that bond survives and phenol is formed. The iodide attacks the benzylic CH2 instead, giving benzyl iodide.

Options giving iodobenzene, benzene or toluene would need the strong aryl C-O bond to break or the benzyl group to be reduced, which does not happen with HI under these conditions.

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