Question

Alcohols (R – OH), phenols (Ar – OH) and carboxylic acids (R – COOH) can undergo ionization of O – H bond to give away proton H⁺; yet they have different pK_a  values, which are 16, 10 and 4.5 respectively. Explain.

Answer 1

pK_a value is indicative of acid strength. Lower of pK_a value stronger the acid. Alcohols, phenols and carboxylic acids, all involve ionization of an O – H bond. But their different pK_a values indicate that their acid strengths are different. This is because the resulting conjugate bases are stabilized to different extents.

As the conjugate base of carboxylic acid is best stabilized, among the three, carboxylic acids are strongest and have the lowest pKa value. As conjugate base of alcohols is destabilized, alcohols are weakest acids and have highest pIQ value. As conjugate base of phenols is moderately stabilized, phenols are moderately acidic and have intermediate pBQ value.