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Sunday, January 19, 2020

Why does aqueous sodium bicarbonate solution dissolve carboxylic acids but not phenol though they are also acidic ?

In both cases the product formed is carbonic acid (pKa=6) which is stronger acid than phenols (pKa=10) but weaker than carboxylic acid(pKa=4.5).
Acid-base equilibrium in second case shift more towards backward direction. Hence phenol does not react with NaHCO3.

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