The correct order of decreasing acid strength of acetic acid (A), for…

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Carboxylic acids are weaker than mineral acids, but they are stronger acids than alcohols and many simple phenols (\(pK_a\) is ∼16 for ethanol and 10 for phenol). The higher acidity of carboxylic acids as compared to phenols can be understood similarly. The conjugate base of carboxylic acid, a carboxylate ion, is stabilised by two equivalent resonance structures in which the negative charge is at the more electronegative oxygen atom. The conjugate base of phenol, a phenoxide ion, has non-equivalent resonance structures in which the negative charge is at the less electronegative carbon atom. Further, the negative charge is delocalized over two electronegative oxygen atoms in carboxylate ion whereas it is less effectively delocalized over one oxygen atom and less electronegative carbon atoms in phenoxide ion. Thus, the carboxylate ion is more stabilised than phenoxide ion, so carboxylic acids are more acidic than phenols.

Effect of substituents on the acidity of carboxylic acids: substituents may affect the stability of the conjugate base and thus, also affect the acidity of the carboxylic acids. Electron withdrawing groups increase the acidity of carboxylic acids by stabilising the conjugate base through delocalisation of the negative charge by inductive and /or resonance effects. Conversely, electron donating groups decrease the acidity by destabilising the conjugate base.