JEE Main 2023 · 6 April · evening · Single correct · +4 / −1

The strongest acid from the following is

  1. (a)
    Option (a)
  2. (b)
    Option (b)
  3. (c)
    Option (c)
  4. (d)
    Option (d)
Answer and solution

Answer (b)

Solution

Chemistry ma’am · 4 steps

Judge each phenol by its phenoxide ion: the group that pulls the negative charge away best wins.

  1. Look at the anion. A phenol is acidic because losing H⁺ gives a phenoxide ion, ArO⁻. Anything that spreads out or pulls away that negative charge makes the ion more stable, so the phenol becomes a stronger acid.
  2. Meta means inductive. All three groups here sit at the meta position. From meta, resonance cannot place charge on the ring carbon that carries the substituent, so only the inductive effect matters. A -I group raises acidity and a +I group lowers it.
    OptionGroup at metaEffect on phenoxidepKₐ
    (a) m-cresol-CH₃, +Ipushes in charge, destabilises10.1
    (c) phenolnonereference10.0
    (d) m-chlorophenol-Cl, -Ipulls charge, stabilises9.1
    (b) m-nitrophenol-NO₂, strong -Ipulls charge most strongly8.4
  3. Why nitro beats chloro. In -NO₂ the nitrogen carries a formal positive charge and is bonded to two electronegative oxygens. That makes its -I pull much stronger than that of a single Cl atom.
  4. So. The order of acidity is m-nitrophenol > m-chlorophenol > phenol > m-cresol. The strongest acid is (b), m-nitrophenol.

The idea to keep. For substituted phenols, stabilise the phenoxide ion. At meta only -I or +I counts. At ortho and para, -R groups such as -NO₂ add a resonance boost on top.

Answer from the NTA final answer key. Solution by PrepWiser.

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Asked about 180 times in JEE Main since 2020. This question is from 2023.