JEE Main 2021 · 25 February · morning · Single correct · +4 / −1

Compound(s) which will liberate carbon dioxide with sodium bicarbonate solution is/are :

JEE Main PYQ figure
  1. (a) C only
  2. (b) B only
  3. (c) B and C only
  4. (d) A and B only
Answer and solution

Answer (c) B and C only

Solution

Chemistry ma’am · 3 steps

Compare each compound with carbonic acid: anything stronger than it pushes CO₂ out of bicarbonate.

  1. The test. RH + NaHCO₃ → RNa + H₂CO₃, and H₂CO₃ then breaks into H₂O + CO₂. This goes forward only if the compound is a stronger acid than H₂CO₃, whose pKₐ is about 6.4.
    CompoundSubstituent effectApprox. pKₐStronger than H₂CO₃?
    A: 2,4,6-triaminophenolthree -NH₂ groups donate electrons (+R) and destabilise the phenoxide ionabove 10, weaker than phenolNo
    B: benzoic acidcarboxylate charge shared equally over two O atoms4.2Yes
    C: 2,4,6-trinitrophenol (picric acid)three -NO₂ groups at ortho and para pull charge away (−R, −I) and stabilise the phenoxide ion0.4Yes
  2. Why A fails. Plain phenol (pKₐ ≈ 10) is already too weak to react with NaHCO₃. Electron-donating amino groups make A even weaker, so no CO₂ is released.
  3. So. Only B and C are stronger acids than carbonic acid, so both give brisk effervescence of CO₂. The answer is (c).

The idea to keep. The bicarbonate test is a strength contest with H₂CO₃ (pKₐ ≈ 6.4). Carboxylic acids and phenols carrying strong −R groups like several -NO₂ win; ordinary or electron-rich phenols lose.

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

Study General Organic Chemistry (GOC)

Asked about 180 times in JEE Main since 2020. This question is from 2021.