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JEE Main levelSingle correct optionDifficulty 2 of 3ap252

The compound shown is treated with chloroform and aqueous sodium hydroxide at 340 K, and the mixture is then acidified. Which structure is the major product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: A

The compound is 4-methylphenol (p-cresol). In the Reimer-Tiemann reaction dichlorocarbene attacks the phenoxide ring at an ortho position, since para is blocked by the methyl group. After hydrolysis the product is 2-hydroxy-5-methylbenzaldehyde. The acid is the Kolbe-Schmitt type product, and the formyl group is not meta to the hydroxyl.
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