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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Identify the correct order of acidic strength for the following compounds: (I) (II) (III)

Options

  1. AIII > II > I
  2. BI > II > III
  3. CII > I > III
  4. DI > III > II

Correct answer

B. I > II > III

Step-by-step solution

The acidic strength of benzoic acid derivatives depends on the stability of the carboxylate anion formed after losing a proton. In compound (III) (benzoic acid), there is no extra stabilization of the conjugate base other than resonance with the benzene ring. In compound (II) (salicylic acid or 2-hydroxybenzoic acid), the conjugate base is stabilized by intramolecular hydrogen bonding between the ortho-hydroxyl group and the carboxylate oxygen. This makes it significantly more acidic than benzoic acid (III). In com

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