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JEE Main levelSingle correct optionDifficulty 2 of 3hx270

The compound shown is heated with aqueous at about 433 K and the mixture is then acidified. Which structure is the main organic product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: C

A single para nitro group activates the ring towards nucleophilic aromatic substitution, but only under forcing conditions (about 433 K). Hydroxide replaces chlorine, giving 4-nitrophenol after acidification. The meta-nitrophenol would need rearrangement, 4-nitroaniline needs ammonia, and 4-chlorophenol would require loss of the nitro group.
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