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Explain the acidic nature of phenols....

Explain the acidic nature of phenols.

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Phenols react with active metal like sodium to forin sodium phenoxide.
`2C_(6)H_(5)OH_2Na to 2C_(6)H_(5)ONa_H`
Phenols react with aqueous sodium hydroxide to form sodium phenoxide.
`C_(6)H_(5)OH+NaOH to C_(6)H_(5)ONa+H_(2)O`
The above reactions shows that phenols are acidic in nature, Le. phenols are Bronsted acids.
The acidic nature of phenol is due to :
• The hydroxyl group ir phenol is directly attached to `sp^(2)` hylbridised carbon of benzene ring which acts as an electron withdrawing group. Due to this phenol easily donates hydrogan ion.
• The phenoxide ion is more stable due to resonance stabilisation and hence it favours the ionisation of phenols.
• The electron withdrawing group increases the acidity of phenols.
Ex: Nitrophenols are more acidic than phenols.
• The electron donating group decreases the acidity of phenols.
Ex, Cresols are less acidic than phenols.
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Knowledge Check

  • Which of the following orders is true regarding the acidic nature of phenol?

    A
    Phenol `gt` O-cresol `gt` O-nitrophenol
    B
    O-cresol `lt` phenol `lt` O-nitrophenol
    C
    phenol `lt` 0-cresol `gt` O-nitrophenol
    D
    phenol `lt` O-cresol `lt` O-nitrophenol III
  • Which of the following orders is true regarding the acidic nature of phenol?

    A
    `"Phenol" gt "o-cresol" gt o-"nitrophenol"`
    B
    `"o-cresol" lt "Phenol" lt o-"nitrophenol"`
    C
    `"Phenol" lt "o-cresol" gt o-"nitrophenol"`
    D
    `"Phenol" lt "o-cresol" lt o-"nitrophenol"`
  • Which of the following order is true regarding the acidic nature of phenol ?

    A
    Phenol `gt` o-cresol `gt` o-nitrophenol
    B
    O-crenol `lt` phenol `lt` o-nitrophenol
    C
    phenol `gt` o-cresol `gt` o-nitrophenol
    D
    phenol `lt` o-cresol `lt` nitrophenol
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