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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Consider the following nucleophilic aromatic substitution reactions: (I) (II) (III) Choose the correct order of reactivity for these reactions.

Options

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

Correct answer

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

Step-by-step solution

The given reactions proceed via the nucleophilic aromatic substitution ( S_NAr ) mechanism. In an S_NAr reaction, the rate-determining step is the addition of the nucleophile to the halogen-bearing carbon to form a carbanion intermediate (Meisenheimer complex). The carbon-halogen bond breaking is not involved in this slow step. The reactivity is governed by the electron-withdrawing inductive effect ( -I effect) of the halogen, which increases the electrophilicity of the carbon atom and stabilizes the intermediate c

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