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JEE Advanced levelSingle correct optionDifficulty 3 of 3el275

The compound shown is hydrolysed with hot dilute acid. Which pair of fragments forms?

  1. AChloroacetic acid and a nitroaniline
  2. BAcetic acid and a dichloro amine
  3. CDichloroacetic acid and a primary amine bearing a nitrophenyl diol unit
  4. DDichloroacetaldehyde and nitrobenzene

Answer: C

The compound shown is chloramphenicol. The only readily hydrolysed group is the amide, which gives dichloroacetic acid and 2-amino-1-(4-nitrophenyl)propane-1,3-diol (as ammonium salt). The aryl nitro group and the alcohols are untouched.
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