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p -Cresol (4-methylphenol) is subjected to two separate reactions: Reaction 1: p -cresol reacts with CHCl ₃ and aqueous NaOH , followed by acidification to yield major product A. Reaction 2: p -cresol reacts with Br ₂ in CS ₂ at 273 K to yield major product B. Identify the major products A and B.

Options

  1. AA is 2-hydroxy-5-methylbenzoic acid; B is 2,6-dibromo-4-methylphenol
  2. BA is 5-hydroxy-2-methylbenzaldehyde; B is 3-bromo-4-methylphenol
  3. CA is 2-hydroxy-5-methylbenzaldehyde; B is 2-bromo-4-methylphenol
  4. DA is 2-hydroxy-5-methylbenzaldehyde; B is 2,6-dibromo-4-methylphenol

Correct answer

C. A is 2-hydroxy-5-methylbenzaldehyde; B is 2-bromo-4-methylphenol

Step-by-step solution

In p -cresol, the - OH group is strongly activating and ortho/para directing, whereas the - CH ₃ group is weakly activating and ortho/para directing. The directing effect of the - OH group dominates. Since the para position is blocked by the - CH ₃ group, electrophilic substitution must occur at the position ortho to the - OH group. Reaction 1 is the Reimer-Tiemann reaction, which introduces a formyl group ( - CHO ) ortho to the - OH group. Thus, product A is 2-hydroxy-5-methylbenzaldehyde. Reaction 2 is brominatio

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