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

Correct answer

B. (I) > (III) > (II)

Step-by-step solution

Nucleophilic aromatic substitution ( S_NAr ) proceeds via an addition-elimination mechanism, forming a carbanion intermediate (Meisenheimer complex). The reactivity depends on two main factors: 1. The presence of electron-withdrawing groups (EWGs) at ortho and para positions, which stabilize the intermediate carbanion and increase reactivity. Conversely, electron-donating groups (EDGs) destabilize the intermediate and decrease reactivity. 2. The nature of the leaving group. For S_NAr , the reactivity order of halog

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