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Which of the following compounds is least likely to give effervescence of $$CO_2$$ in presence of aq. NaHCO$$_3$$?
Effervescence of $$CO_2$$ with aqueous $$NaHCO_3$$ is observed only when the organic compound can donate a proton more acidic than the first proton of carbonic acid $$H_2CO_3$$.
The equilibrium that decides the test is
$$\text{HA} + NaHCO_3 \;\rightleftharpoons\; NaA + H_2CO_3 \;\rightleftharpoons\; NaA + CO_2\uparrow + H_2O$$
For the reaction to proceed to the right, the acid strength order must be $$\text{p}K_a(\text{HA}) \lt \text{p}K_a(H_2CO_3)\;( \approx 6.4 ).$$
Now examine each option:
Case A: Benzoic acid, $$C_6H_5COOH$$Thus the compound least likely to give effervescence of $$CO_2$$ with aqueous $$NaHCO_3$$ is the phenol in Option D.
Final answer: Option D which is: p-Cresol (or any phenolic compound shown in Option D).
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