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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

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

Options

  1. AII > III > I
  2. BII > I > III
  3. CI > III > II
  4. DI > II > III

Correct answer

B. II > I > III

Step-by-step solution

The acidic strength of a compound depends on the stability of its conjugate base. Let us analyze the conjugate bases of the given compounds: 1. Compound (II) is benzenesulfonic acid. Its conjugate base, the benzenesulfonate ion ( Ph-SO ₃^- ), is highly stabilized by three equivalent resonance structures, dispersing the negative charge over three highly electronegative oxygen atoms. 2. Compound (I) is benzoic acid. Its conjugate base, the benzoate ion ( Ph-COO ^- ), is stabilized by two equivalent resonance structur

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