Question 12.20: Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Why?
Question 12.20: Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Why?

Solution:

The phenoxide ion has the following resonance structures:

The resonance structures of the phenoxide ion show that less electronegative carbon atoms carry a negative charge in II, III, and IV. As a result, these three configurations have a minor impact on the phenoxide ion’s resonance stability.

As a result, these structures can be removed. The structures I and V of the more electronegative oxygen atom contain negative charge.

Resonance structures of carboxylate ion are:

Resonating structures I′ and II′ have a charge carried by a more electronegative oxygen atom in the case of carboxylate ion.

In resonant structures I′ and II′, the negative charge is also delocalized over two oxygen atoms. The negative charge is concentrated on the same oxygen atom in the phenoxide ion’s resonant structures I and V. As a result, its stability is influenced more by carboxylate ion resonating structures than phenoxide ion resonating structures. As a result, the resonance stability of the phenoxide ion is lower than that of the carboxylate ion. As a result, carboxylic acid is a more powerful acid than phenol.