Acidic Strength of Following compounds- JEE/NEET concepts/questions

1.

The compounds are:

  • I = Cyclohexane carboxylic acid
  • II = Tetrahydropyran-2-carboxylic acid (O atom α to the carbon bearing –COOH)
  • III = Tetrahydropyran-3-carboxylic acid (O atom β to the carbon bearing –COOH)

Key Concept

The –I (negative inductive) effect of oxygen increases the acidity of a carboxylic acid by stabilizing the carboxylate ion.

  • The closer the oxygen atom is to the –COOH group, the stronger its –I effect.
  • The inductive effect decreases rapidly with distance.

Comparison

  • II: Oxygen is α to the carbon attached to –COOH → strongest –I effectmost acidic.
  • III: Oxygen is β to the carbon attached to –COOH → weaker –I effect than II → intermediate acidity.
  • I: No oxygen in the ring → no additional –I effect → least acidic.

Acidic strength order

II>III>I\boxed{\text{II} > \text{III} > \text{I}}

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