Concept:Acidity depends on the stability of the conjugate base formed after losing
H+.
Greater the resonance stabilisation of the conjugate base, greater is the acidity.
Explanation:Carboxylic acids lose a proton to form the carboxylate ion:
RCOOH→RCOO−+H+In the carboxylate ion, the negative charge is delocalised equally over two oxygen atoms.
The two resonance structures are equivalent:
RCOO−↔R−C(=O)−O−↔R−C(−O−)=OEqual resonance structures make the carboxylate ion highly stable.
Phenol also forms a conjugate base, the phenoxide ion:
C6​H5​OH→C6​H5​O−+H+In the phenoxide ion, the negative charge is delocalised into the benzene ring.
However, these resonance structures are not equivalent.
In some phenoxide resonance forms, the negative charge is on a carbon atom, which is less stable than on oxygen.
Thus, the carboxylate ion is more resonance stabilised than the phenoxide ion.
A more stable conjugate base means the acid releases
H+ more readily.
Therefore, carboxylic acids are more acidic than phenols.
Answer:Option D: More resonance stabilisation of their conjugate base.