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JEE Main levelSingle correct optionDifficulty 2 of 3hx266

Under conditions (aqueous , 443 K) in which the para-nitro isomer of the compound shown is hydrolysed, the compound shown:

  1. Ais hydrolysed only slightly or not at all, because a meta nitro group cannot delocalise the negative charge of the intermediate onto itself
  2. Bis hydrolysed faster, because the inductive effect is strongest at the meta position
  3. Cis hydrolysed at the same rate, because any nitro group activates the ring equally
  4. Dreacts via a benzyne intermediate to give mainly the meta phenol

Answer: A

The compound is 3-chloronitrobenzene. A nitro group activates nucleophilic aromatic substitution only from the ortho or para positions, where the negative charge of the intermediate can be delocalised onto the nitro group. From the meta position it cannot, so the compound reacts very little or not at all under these conditions.
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