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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx199

p-Cresol (4-methylphenol) is treated with and aqueous and then acidified. The main product is

  1. A2-hydroxy-4-methylbenzaldehyde
  2. B2-hydroxy-5-methylbenzaldehyde
  3. C2-hydroxy-3-methylbenzaldehyde
  4. D4-hydroxy-3-methylbenzaldehyde

Answer: B

Reimer-Tiemann formylation by dichlorocarbene occurs ortho to the phenoxide oxygen; the para position is blocked by . The goes to C-2 relative to OH; the methyl, para to OH, is then at C-5 of the benzaldehyde numbering (CHO = C1, OH = C2).
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