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JEE Advanced levelSingle correct optionDifficulty 3 of 3g2045

Which of the following is the most acidic?

  1. A2,4-dimethylphenol
  2. B4-nitrophenol
  3. C3,5-dinitrophenol
  4. D2,4-dinitrophenol

Answer: D

In 2,4-dinitrophenol both nitro groups are at positions conjugated with the phenoxide oxygen (ortho and para), so both exert -M and -I effects (pKa about 4.1). In 3,5-dinitrophenol both nitro groups are meta and exert only -I (pKa about 6.7). 4-Nitrophenol has pKa 7.15 and 2,4-dimethylphenol is weaker than phenol.
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