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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2155

Chlorobenzene is heated with excess and until dinitration occurs. The major dinitration product is

  1. A1-chloro-2,4-dinitrobenzene
  2. B1-chloro-2,3-dinitrobenzene
  3. C1-chloro-2,6-dinitrobenzene
  4. D1-chloro-3,5-dinitrobenzene

Answer: A

The first nitro group enters mainly para to Cl, giving 1-chloro-4-nitrobenzene. Now Cl directs ortho to itself and the nitro group directs meta, and these positions coincide. The second nitro group enters ortho to Cl and meta to the first nitro group, giving 1-chloro-2,4-dinitrobenzene.
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