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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Identify the correct order of reactivity of the following compounds towards nucleophilic aromatic substitution ( S_NAr ): I. II. III.

Options

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

Correct answer

B. II > I > III

Step-by-step solution

Nucleophilic aromatic substitution ( S_NAr ) is facilitated by the presence of electron-withdrawing groups (such as - NO₂ ) at the ortho and para positions relative to the leaving group (halogen). These groups stabilize the intermediate carbanion (Meisenheimer complex) through strong -I and -M effects. The greater the number of electron-withdrawing groups at the ortho and para positions, the more stable the intermediate, and consequently, the higher the reactivity of the compound towards S_NAr . Analyzing the given

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