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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. A(i) > (ii) > (iii)
  2. B(ii) > (iii) > (i)
  3. C(iii) > (i) > (ii)
  4. D(i) > (iii) > (ii)

Correct answer

A. (i) > (ii) > (iii)

Step-by-step solution

The acidic strength of carboxylic acids is directly proportional to the stability of their conjugate base. Electron-withdrawing groups (EWGs) increase acidity via the -I effect by stabilizing the carboxylate ion, while electron-donating groups (EDGs) decrease acidity via the +I effect. In compound (i), the -NC group is a very strong EWG. Its powerful -I effect strongly stabilizes the conjugate base, making it the most acidic among the given compounds. In compound (ii), the -Cl group is also an EWG, but its -I effec

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