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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx272

The compound shown reacts with aqueous on warming. Select all correct statements.

  1. AThe negative charge of the intermediate is delocalised onto both nitro groups.
  2. BThe addition of hydroxide to the ring is the slow step.
  3. CThe reaction proceeds through a benzyne intermediate.
  4. DIt is hydrolysed under milder conditions than 4-chloronitrobenzene.

Answer: A, B, D

This is nucleophilic aromatic substitution by the addition-elimination mechanism: hydroxide adds first (rate-determining) to give an anionic intermediate whose charge is delocalised onto the ortho and para nitro groups. Because two such groups are present, the reaction proceeds at a lower temperature than for 4-chloronitrobenzene. No benzyne is involved, since benzyne needs a very strong base such as amide and does not form when the ring is activated for addition.
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