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JEE Main levelSingle correct optionDifficulty 2 of 3g2013

Which of the following is the most acidic?

  1. A3-nitrophenol
  2. B4-nitrophenol
  3. C2,4-dinitrophenol
  4. D4-methylphenol

Answer: C

Nitro groups at the ortho and para positions stabilise the phenoxide ion by both -M and -I effects. 2,4-Dinitrophenol has two such groups (pKa about 4.1), compared with 7.15 for 4-nitrophenol, 8.35 for 3-nitrophenol (only -I) and about 10.2 for 4-methylphenol.
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