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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc162

Toluene is heated with 3 mol of in sunlight, giving a trichloro compound. This is boiled with aqueous and then acidified. The final organic product is

  1. Abenzaldehyde
  2. Bbenzyl alcohol
  3. Cbenzoic acid
  4. D2,4,6-trichlorotoluene

Answer: C

Three chlorines substitute the three benzylic hydrogens: (benzotrichloride). Hydrolysis of the three C-Cl bonds on one carbon gives , which loses water to form the carboxylate. Acidification gives benzoic acid. Benzaldehyde would result from (2 mol of ).
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