Which of the following will not be soluble in sodium hydrogen carbonate?
- 2,4,6-Trinitrophenol
- Benzoic acid
- o-Nitrophenol
- Benzenesulphonic acid
Answer
(3) o-Nitrophenol
Solution
A compound dissolves in NaHCO3 only if it is a stronger acid than carbonic acid (pKa 6.4), liberating CO2.
Benzenesulphonic acid and benzoic acid (pKa 4.2) are strong enough ⇒ soluble.
2,4,6-Trinitrophenol (picric acid, pKa 0.71) has three –I, –R nitro groups ⇒ strongly acidic ⇒ soluble.
o-Nitrophenol (pKa 7.2) is a weaker acid than carbonic acid ⇒ does not dissolve in NaHCO3.
Answer: (3)