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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3102

4-Methylphenol (p-cresol) is heated with and aqueous , and the mixture is then acidified. The major product is

  1. A2-Methyl-4-chlorophenol
  2. B2-Hydroxy-5-methylbenzaldehyde
  3. C2-Hydroxy-5-methylbenzoic acid
  4. D4-Hydroxy-3-methylbenzaldehyde

Answer: B

The Reimer-Tiemann reaction attacks the phenoxide ring with at the ortho position. The para position is blocked by , so the group enters ortho to oxygen, and hydrolysis gives . Numbering from CHO as C-1 with OH at C-2, the methyl (para to OH) sits at C-5.
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