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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3201

3,4-Dichloronitrobenzene (1,2-dichloro-4-nitrobenzene) reacts with one equivalent of sodium methoxide in methanol on warming. The major product is

  1. A4-chloro-2-methoxy-1-nitrobenzene
  2. B1-chloro-2-methoxy-4-nitrobenzene
  3. C2-chloro-1-methoxy-4-nitrobenzene
  4. D1,2-dimethoxy-4-nitrobenzene

Answer: C

Only a chlorine ortho or para to the nitro group is activated for SNAr. In 1,2-dichloro-4-nitrobenzene the Cl on C-1 is para to (C-4), while the Cl on C-2 is meta. Methoxide therefore replaces the C-1 chlorine through a Meisenheimer complex, leaving the meta chlorine untouched.
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