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JEE Main levelSingle correct optionDifficulty 2 of 3o3179

1-Chloro-2,4-dinitrobenzene is stirred with hydrazine () in ethanol. The main product is

  1. A1-chloro-2-hydrazinyl-4-nitrobenzene
  2. B2,4-dinitroaniline
  3. C(2,4-dinitrophenyl)hydrazine
  4. D2,4-dinitrophenol

Answer: C

The ring carbon bearing Cl is ortho and para to two nitro groups, so hydrazine adds there and chloride is lost (SNAr). The nitro groups are not displaced because the Meisenheimer complex needs the nitro groups to stabilise the charge. The product is . Phenol or aniline would need water or ammonia as the nucleophile.
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