Which of the following compounds is least likely to give effervescence of CO2 in presence of aq. NaHCO3?
- Ph- NH3 Cl
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Answer
(4) [figure]
Solution
HA + NaHCO3 NaA + H2O + CO2 occurs only when HA is a stronger acid than H2CO3 (pKa 6.4).
(1) Anilinium chloride: C6H5 NH3 is the conjugate acid of the weak base aniline (pKa 4.6) stronger than H2CO3 CO2 evolved.
(2) 4-Nitrobenzoic acid (pKa 3.4): a carboxylic acid, made stronger by the electron-withdrawing -NO2 group CO2 evolved.
(3) Picric acid, 2,4,6-trinitrophenol (pKa 0.4): three -NO2 groups (–R, –I) make it a strong acid CO2 evolved.
(4) 3-Nitrophenol (pKa 8.4): a meta -NO2 group acts only by –I effect, so it is still weaker than H2CO3 no CO2.
Answer: (4)