Q. Among the following compounds, the most acidic is

A) $p$-nitrophenol
B) $p$-hydroxybenzoic acid
C) $o$-hydroxybenzoic acid
D) $p$-toluic acid
Explanation

(c)
A monosubstituted benzoic acid is stronger than a monosubstituted phenol as former being a carboxylic acid. Among the given substituted benzoic acid, $ortho -$ hydroxy acid is strongest acid although – OH causes electron donation by resonance effect which tends to decreases acid strength. It is due to very high stabilisation of conjugate base by intramolecular H-bond which outweight the electron donating resonance effect of – OH.
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The overall order of acid-strength of given four acids is $ortho$-hydroxybenzoic acid $\left( pK_{a} = 2.98 \right) >$ Toluic acid $pk_{a} = 4.37) > p -$hydroxybenzoic acid
$\left( pk_{a} = 4.58 \right) > p -$nitrophenol $(pk_{a} = 7.15)$.

Dr. Abubacker
Reviewed by Dr. Abubacker

Physics Educator & NEET/JEE Specialist

Ph.D. in Physics with 19+ years of teaching experience.