JEE Main 2021 · 25 February · morning · Single correct · +4 / −1
Compound(s) which will liberate carbon dioxide with sodium bicarbonate solution is/are :
- (a) C only
- (b) B only
- (c) B and C only
- (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.
- 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.
Compound Substituent effect Approx. pKₐ Stronger than H₂CO₃? A: 2,4,6-triaminophenol three -NH₂ groups donate electrons (+R) and destabilise the phenoxide ion above 10, weaker than phenol No B: benzoic acid carboxylate charge shared equally over two O atoms 4.2 Yes C: 2,4,6-trinitrophenol (picric acid) three -NO₂ groups at ortho and para pull charge away (−R, −I) and stabilise the phenoxide ion 0.4 Yes - 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.
- 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.