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When the mixed ether phenyl benzyl ether (C6H5-O-CH2-C6H5) is treated with excess HI, which products are formed?

1. C6H5-CH2-I (benzyl iodide)
2. C6H5-CH2-OH (benzyl alcohol)
3. C6H5-I (iodobenzene)
4. C6H5-OH (phenol)

Correct answer: C6H5-OH (phenol)

Solution

HI cleaves the weaker alkyl C-O bond. The oxygen stays with the arene to give phenol (C6H5OH), while the benzyl group leaves as benzyl iodide (C6H5CH2I). Both products form, but phenol is listed among the options.

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