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JEE Main levelSingle correct optionDifficulty 2 of 3hx156

In the reaction of 1-X-2,4-dinitrobenzene with sodium methoxide in methanol, the order of reactivity for X = F, Cl, Br, I (same conditions) is such that the most reactive substrate is

  1. Athe fluoro compound, because the strongly electronegative stabilises the Meisenheimer intermediate formed in the rate-determining addition step
  2. Bthe chloro compound, because is the best compromise between bond strength and size
  3. Cthe iodo compound, because is the weakest bond
  4. Dall four react at the same rate because the leaving group is not involved at all

Answer: A

In SNAr the slow step is attack of the nucleophile to form the anionic sigma complex, not the loss of . A more electronegative halogen increases the electrophilicity of the ipso carbon and stabilises the complex, so F is the most reactive (F > Cl Br > I), opposite to the trend in of alkyl halides.
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