Final answer:
Carboxylic acids are stronger acids than phenols due to better charge delocalization over oxygen atoms in the carboxylate ion and inductive effects that weaken the O-H bond.
Step-by-step explanation:
Although the phenoxide ion has more resonating structures than the carboxylate ion, carboxylic acid is a stronger acid than phenol. The reason for this is primarily due to the fact that the negative charge in the carboxylate ion is delocalized over two electronegative oxygen atoms, which is more effective in stabilizing the conjugate base than sharing the negative charge with the less electronegative carbons in phenol. Additionally, there are inductive effects at play, which pull electron density away from the acidic hydrogens, making them more easily dissociable, thus contributing to the acid strength.