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Explain the acidic nature of phenols and...

Explain the acidic nature of phenols and compare with that of alcohols.

Text Solution

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The reaction of phenol with sodium metal and with aq. NaOH indicates the acidic nature of phenol.
i) Phenol reacts with sodium metal to form sodium phenoxide.

`to` In phenol hydroxyl group is attached to the `Sp^(2)` hydridised carbon of benzene ring which acts as electron with drawing group.
Comparison of acidic character of Phenol and Ethanol :
`to` The reaction of phenol with aq. NaOH indicates that phenols are stronger acids than alcohols.
`to` The hydroxyl group attached to an aromatic ring is more acidic than in hydroxyl group is attached to an alkyl group. `to` Phenol forms stable phenoxide ion stabilised by resonance but ethoxide ion is not.

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Knowledge Check

  • The acidic character of phenol is due to

    A
    Greater resonance stabilization of phenoxide ion over phenol
    B
    Greater resonance stabilization of phenol over phenoxide ion
    C
    Because of tautomerism occurring in phenol
    D
    Because oxygen is more electronegative than hydrogen
  • The acidic character of phenol is due to

    A
    Greater resonance stabilization of phenoxide ion over phenol
    B
    Greater resonance stabilization of phenol over phenoxide ion
    C
    Because of tautomerism occurring in phenol
    D
    Because oxygen is more electronegative than hydrogen
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