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NEET CHEMISTRYMedium

The compound, among the following, that will not be soluble in sodium hydrogen carbonate is:

A

2, 4, 6-Trinitrophenol

B

Benzoic acid

C

o-Nitrophenol

D

Benzenesulphonic acid

Step-by-Step Solution

Sodium hydrogen carbonate (NaHCO3NaHCO_3) is a weak base. It reacts with acids that are stronger than carbonic acid (H2CO3H_2CO_3) to release CO2CO_2 and form soluble sodium salts.

  1. Benzenesulphonic acid and Benzoic acid are much stronger acids than carbonic acid, so they dissolve in NaHCO3NaHCO_3.
  2. 2, 4, 6-Trinitrophenol (Picric acid): Although it is a phenol, the presence of three strong electron-withdrawing nitro groups (NO2-NO_2) makes it more acidic than carbonic acid. Thus, it is soluble.
  3. o-Nitrophenol: Phenols are generally weaker acids than carbonic acid. While the nitro group increases acidity, a single NO2-NO_2 group (especially with intramolecular hydrogen bonding in the ortho isomer) does not make it acidic enough to displace CO2CO_2 from NaHCO3NaHCO_3. Therefore, it remains insoluble.
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