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JEE Main levelSingle correct optionDifficulty 2 of 3hc206

Toluene is treated with excess chlorine in sunlight at its boiling point, and the product is hydrolysed with hot aqueous alkali followed by acidification. The final organic product is:

  1. ABenzyl alcohol
  2. BBenzaldehyde
  3. CBenzoic acid
  4. Do-Chlorotoluene

Answer: C

Radical chlorination of the methyl group proceeds to . Hydrolysis of the trichloromethyl group gives the carboxylic acid (via the unstable ), so benzoic acid is formed.
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