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JEE Advanced · Chemistry · 13. GOC

Among the following compounds, the most acidic is

  1. A p-nitrophenol
  2. B p-hydroxybenzoic acid
  3. C o-hydroxybenzoic acid
  4. D p-toluic acid
Verified Solution

Answer & Solution

Correct Answer

(C) o-hydroxybenzoic acid

Step-by-step Solution

Detailed explanation

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 - \(\mathrm{OH}\) cause electron donation by resonance effect which tends to decrease acid strength. It is due to a very high stabilization of conjugate base by intramolecular \(\mathrm{H}\)-bond which outweight the electron donating resonance effect of \(-\mathrm{OH}\).

The overall order of acid-strength of given four acids is ortho-hydro \(x y\) benzoic acid \(\left(p K_a=298\right)>\) Toluic acid \(\left.p K_a=4.37\right)>p\)-hydroxybenzoic acid \(\left(p K_a=4.58\right)>\) \(p\)-nitrophenol \(\left(p K_a=7.15\right)\).
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