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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(III) > (I) > (II)
  3. C(I) > (III) > (II)
  4. D(II) > (III) > (I)

Correct answer

A. (I) > (II) > (III)

Step-by-step solution

In nucleophilic aromatic substitution ( S_NAr ), the reaction proceeds via a two-step mechanism where the first step is the addition of the nucleophile to the halogen-bearing carbon to form a negatively charged intermediate (Meisenheimer complex). This step is the slow and rate-determining step. The reactivity of the aryl halide depends on the stability of this intermediate carbanion. The more stabilized the negative charge, the faster the reaction. Halogens stabilize the intermediate through their electron-withdra

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