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COMPARISON OF
ACIDITY
Phenols are much more acidic than alcohols because the negative charge in the
phenoxide ion is not localized on the oxygen atom as it is in an alkoxide ion but is
delocalized as it is shared by a number of carbon atoms in benzene ring.
Oxygen is electronegative, much more than carbon. In acetate, the
negative charge is delocalized onto both oxygens, which happen to
be the electronegative atoms.
In phenoxide, the charge is trying to delocalize onto carbons which
just aren't that electronegative. So phenoxide is less stabilized by
resonance, and phenol is a weaker acid.
In Benzoic acid negative charge is present at the more
electronegative oxygen atom. Where as in conjugate base of phenol
phenoxide ion the negative charge is on less electronegative carbon
atom . Thus the benzoate ion is more stable than phenoxide ion .So
benzoic acid is more more acidic than phenol.
Comparison of Acidity in organic chemistry

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Comparison of Acidity in organic chemistry

  • 2. Phenols are much more acidic than alcohols because the negative charge in the phenoxide ion is not localized on the oxygen atom as it is in an alkoxide ion but is delocalized as it is shared by a number of carbon atoms in benzene ring.
  • 3. Oxygen is electronegative, much more than carbon. In acetate, the negative charge is delocalized onto both oxygens, which happen to be the electronegative atoms. In phenoxide, the charge is trying to delocalize onto carbons which just aren't that electronegative. So phenoxide is less stabilized by resonance, and phenol is a weaker acid.
  • 4. In Benzoic acid negative charge is present at the more electronegative oxygen atom. Where as in conjugate base of phenol phenoxide ion the negative charge is on less electronegative carbon atom . Thus the benzoate ion is more stable than phenoxide ion .So benzoic acid is more more acidic than phenol.