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Phenyl methyl ether (on anisole) reacts ...

Phenyl methyl ether (on anisole) reacts with HI to give phenol and methyl iodide and not iodobenzene and methyl alcohol. Justify .

Text Solution

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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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Knowledge Check

  • Ethyl methyl ether is

    A
    Solid
    B
    Gas
    C
    Liquid
    D
    Colloid

  • Tert-butyl methyl ether on reaction with HI will give

    A
    `CH_3I + (CH_3)_3COH`
    B
    `CH_3I+(CH_3)_3C-I`
    C
    `CH_3OH+(CH_3)_3C-I`
    D
    `CH_3OH+(CH_3)_3-OH`

  • The reaction of anisole with HI gives phenol rather than iodobenzene because

    A
    the bond between `O-CH_3 is weaker than O-C_6H_5`
    B
    the carbon of phenyl group is `sp2-hybridised` and has a partial double bond character
    C
    Both (1) and (2)
    D
    None of the above

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