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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g2042

Which of the following statements are correct? (Use pKa values: 4-nitrophenol 7.15, 3-nitrophenol 8.35, phenol 10.0, 2,4,6-trinitrophenol 0.4, carbonic acid pKa1 6.4.)

  1. A4-Nitrophenol is a stronger acid than 3-nitrophenol because -M effect operates in the para isomer in addition to -I effect.
  2. B2,4,6-Trinitrophenol is more than times as strong an acid as phenol.
  3. CCyclohexanol is a stronger acid than phenol because the alkyl ring donates electrons to oxygen.
  4. DPhenol dissolves in aqueous NaOH but not to a significant extent in aqueous .

Answer: A, B, D

Statement 1: true (resonance onto nitro oxygens). Statement 2: , true. Statement 3: false, the donor effect destabilises the alkoxide and cyclohexanol (pKa about 16) is weaker than phenol. Statement 4: true, because hydrogencarbonate is the conjugate base of carbonic acid (pKa 6.4), which is much stronger than phenol.
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