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COMEDK · Chemistry · 28. Carboxylic Acid Derivatives

Which one of the following correctly represents the decreasing order of acidic nature of the given carboxylic acids:
[A] 2-Hydroxybenzoic acid
[B] Benzoic acid
[C] 3-Hydroxybenzoic acid
[D] 4- Hydroxybenzoic acid

  1. A \([\mathrm{A}]>[\mathrm{C}]>[\mathrm{B}]>[\mathrm{D}]\)
  2. B \([\mathrm{D}]>[\mathrm{C}]>[\mathrm{B}]>[\mathrm{A}]\)
  3. C \([\mathrm{D}]>[\mathrm{B}]>[\mathrm{C}]>[\mathrm{A}]\)
  4. D \([\mathrm{B}]>[\mathrm{A}]>[\mathrm{C}]>[\mathrm{D}]\)
Verified Solution

Answer & Solution

Correct Answer

(A) \([\mathrm{A}]>[\mathrm{C}]>[\mathrm{B}]>[\mathrm{D}]\)

Step-by-step Solution

Detailed explanation

The acidity of substituted benzoic acids is determined by the electronic effects of the substituents. The -OH group exerts both an electron-withdrawing inductive effect (-I) and an electron-donating resonance effect (+M). In 2-hydroxybenzoic acid (salicylic acid), the…