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Phenols are more acidic than alcohols be...

Phenols are more acidic than alcohols because

A

phenoxide ion is stabilized by resonance

B

phenols are more soluble in polar solvents

C

phenoxide ions do not exhibit resonance

D

alcohols do not lose `H` atoms at all

Text Solution

Verified by Experts

The correct Answer is:
A

Three out of five resonating structures for phenol carry both positive and negative charge while all the resonating structures for phenoxide ion carry only a negative charge, Since energy must be supplied to secparte oppsite charges. Tge structyres for the phenol should contain more energy and hence be less stabe than be the structures or phenoxide ion.
Thus the net effect if resonance us ti stabilize the phenoxide ionn to a greater extent than the phenol. This shifts the equilibrium towards ionization and makes `K_(a)` larger than for an alcohol.

In short we can say that the ionization constant of phenol is higher than that of ethanol because phenoxide ion is tabilized through delocalisation.
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Knowledge Check

  • Phenol are more acidic than alcohols because

    A
    phenoxide ion is stabilised by resonance
    B
    phenols are more soluble in polar solvents
    C
    phenols ions do not exhibit resonance
    D
    alcohols donot lose H atoms at all.
  • Phenol is more acidic than alcohol because :

    A
    phenol is more soluble in polar solvents
    B
    alcohol does not lose hydrogen atom
    C
    phenoxide ion is stabilised by resonance
    D
    phenoxide ion does not exhibit resonance
  • Phenols are more acidic than alcohols and CH_(3)NO_(2) because

    A
    B
    which is the conjugate base of phenol is more stable than `Coverset(Ө)H_(2)-NO_(2)`
    C
    D
    In the phenoxide , the negative charge is on oxygen atom having greater unoccupied surface volume than in `Coverset(Ө)H_(2)-NO_(2)` where the -ve charge is on a lesser unoccupied surface volume of carbon thereby making
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