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Fundamentals of Organic ChemistryChemistryAmines

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

Options

  1. A(II) > (III) > (I)
  2. B(I) > (II) > (III)
  3. C(I) > (III) > (II)
  4. D(III) > (I) > (II)

Correct answer

C. (I) > (III) > (II)

Step-by-step solution

The nucleophilicity of pyridine derivatives depends on the availability of the lone pair of electrons on the nitrogen atom. Electron-donating groups (EDG) increase the electron density on the nitrogen atom, thereby increasing nucleophilicity. Conversely, electron-withdrawing groups (EWG) decrease the electron density on the nitrogen atom, decreasing nucleophilicity. In compound (I), the - CH ₃ group acts as an EDG through +I and hyperconjugation effects, making it the strongest nucleophile among the given compounds

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