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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2272

The compound shown is brominated with and . Select all correct statements.

  1. AThe major product has Br ortho to the methyl group.
  2. BChlorine is ring-deactivating but still ortho/para-directing because of lone-pair donation.
  3. CThe methyl group controls the orientation because it is the stronger activator.
  4. DSubstitution ortho to Cl and ortho to give the same compound.

Answer: A, B, C

The compound is 4-chlorotoluene. The activating methyl group outweighs the weakly deactivating chlorine in controlling orientation, so Br enters ortho to (2-bromo-4-chlorotoluene). Chlorine withdraws inductively (deactivating) but donates a lone pair by resonance, which directs ortho/para. The two possible products are different compounds, so D is false.
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