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Q 12.20 Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Why?
Answers (2)
In carboxylate ion the electron is delocalised between oxygen, which is electronegative in nature. But in case of phenoxide ion, the electron are delocalise between less electronegative atom and also phenoxide ion has non-equivalent resonance structure. Therefore, carboxylate ion is more resonance stable than phenoxide ion and we know that more stable the conjugate base of an acid, high strong is the acidic
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It can be observed from the resonance structures of phenoxide ion that in II, III and IV, less electronegative carbon atoms carry a negative charge. Therefore, these three structures contribute negligibly towards the resonance stability of the phenoxide ion. Hence, these structures can be eliminated. Only structures I and V carry a negative charge on the more electronegative oxygen atom.
Further, in resonating structures I' and II', the negative charge is delocalized over two oxygen atoms. But in resonating structures I and V of the phenoxide ion, the negative charge is localized on the same oxygen atom. Therefore, the resonating structures of carboxylate ion contribute more towards its stability than those of phenoxide ion. As a result, carboxylate ion is more resonance-stabilized than phenoxide ion. Hence, carboxylic acid is a stronger acid than phenol.
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