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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap262

Which order correctly places the compound shown, phenol, 4-methylphenol and 2,4-dinitrophenol in decreasing acid strength?

  1. A2,4-dinitrophenol > the compound shown > phenol > 4-methylphenol
  2. BThe compound shown > 2,4-dinitrophenol > phenol > 4-methylphenol
  3. C2,4-dinitrophenol > phenol > the compound shown > 4-methylphenol
  4. D4-methylphenol > phenol > the compound shown > 2,4-dinitrophenol

Answer: A

The compound is 3-nitrophenol ( about 8.4). Two nitro groups, one of them ortho and one para, give 2,4-dinitrophenol ( about 4.1). Phenol is about 10.0, and the electron-donating methyl group in 4-methylphenol (about 10.3) makes it the weakest. The order is therefore 2,4-dinitrophenol > 3-nitrophenol > phenol > 4-methylphenol.
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