1)

Among the foliowing compounds, the most acidic is


A) p-nitrophenol

B) p-hydroxybenzoic acid

C) o-hydroxybenzoic acid

D) p-toluic acid

Answer:

Option C

Explanation:

A monosubstituted benzoic acid is stronger than a monosubstituted phenol as the former is a carboxylic acid. Among the given substituted benzoic acid, ortho-hydroxy acid is the strongest acid although -OH causes electron donation by resonance effect which tends to decrease acid strength. It is due to a very high stabilization 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-hydro xy benzoic acid

$(pK_{a}=2.98)>$ Toluic acid  $pK_{a}=4.37) >$ p-hydroxybenzoic acid  $(pK_{a}=4.58)>$

p-nitrophenol  $(pK_{a}=7.15)$