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

Correct answer

C. (i) > (iii) > (ii)

Step-by-step solution

Boronic acids act as Lewis acids by accepting an OH^- ion from water to form a tetrahedral boronate anion, ArB(OH)₃^- . The acidic strength increases with the presence of electron-withdrawing groups, which increase the electron deficiency of the boron atom and stabilize the resulting conjugate base. The -NO₂ group is a strong electron-withdrawing group that exerts both -I (inductive) and -M (mesomeric) effects. In o-nitrophenylboronic acid (i), the -NO₂ group is at the ortho position. It exerts a strong -I effect d

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