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Phenyl methyl ether reacts with HI to give phenol and methyl iodide and not iodobenzene and methl alcohol. Why? |
Answer» Solution :Protonation of phenyl methyl ether (anisole) gives oxononium ion. In this ion, `O-CH_(3)` bond is weaker than `O-C_(6)H_(5)` bond which has some double bond character DUE to resonance between the lone pair of electrons on the oxygen atom and the `SP^(2)`-HYBRIDIZED carbon atom of the phenyl ring. therefore, ATTACK by `I^(-)` ion exclusively BREAKS the weaker `O-CH_(3)` bond forming methyl iodide and phenol. 
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