Question

Phenate ion has more number of contributing structures than benzoate ion, but still benzoic acid is a stronger acid. Explain.

Answer 1

In phenate ion, the negative charge available is dispersed only one electronegative oxygen atom while there are two oxygen atoms in benzoate ion to disperse the negative charge. This means that benzoate ion is more stable than phenate ion and this makes benzoic acid stronger acid than phenol although the contributing structures for phenate ion (five) are more than for benzoate ion (two).