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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Identify the correct order of reactivity for the S _ N 2 reaction of the following compounds: (i) (ii) (iii)

Options

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

Correct answer

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

Step-by-step solution

The given compounds are derivatives of benzyl chloride undergoing an S _ N 2 reaction. In an S _ N 2 reaction, the rate depends on the electrophilicity of the carbon atom undergoing substitution and the stability of the transition state. The transition state in an S _ N 2 reaction has a partial negative charge on the central carbon atom. Electron-withdrawing groups (EWG) such as - NO ₂ exert -I and -R effects. They withdraw electron density from the benzene ring, which increases the electrophilicity of the benzylic

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