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The pKa of p-nitrophenol is 7.15. Would you expect this substance to dissolve in sodium bicarbonate...

The pKa of p-nitrophenol is 7.15. Would you expect this substance to dissolve in sodium bicarbonate solution? The pKa of 3,6-dinitrophenol is 5.15. Will it dissolve in bicarbonate solution?

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Answer #1

The conjugate acid of sodium bicorbonate is carbonic acid and its pKa value is 6.36 .That means sodium bicarbonate can deprotonate the phenolic proton of 3,6-dinitrophenol and solubilize the ion but not p-nitrophenol .

The reason isif the given acid is relatively weak,its conjugate base is stronger and viceversa

compare pKa if a compound has higher pKa thus it would be more acidic than bicarbonate .Then bicarbonate can not dissolve the compound in an aqueous solution .7.15 is higher than 6.36 so p-nitrophenol is not soluble in bicarbonate and 3,6-dinitrophenol dissolves in bicarbonate solution as its pKa is 5.15 less than bicarbonate solution

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