A mixture of a carboxylic acid and a phenol can often be separated by extracting with aqueous sodium bicarbonate and a suitable organic solvent. What difference in chemical properties of the carboxylic acid and the phenol make this separation possible?

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21-03-2020
Chemistry

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A mixture of a carboxylic acid and a phenol can often be separated by extracting with aqueous sodium bicarbonate and a suitable organic solvent. What difference in chemical properties of the carboxylic acid and the phenol make this separation possible?

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OrethaWilkison OrethaWilkison · Answer 1 · 2020-03-25T10:00:32+01:00

Answer:

Difference in acidity between carboxylic acid and phenol makes their separation possible by aqueous sodium bicarbonate.

Explanation:

[tex]pK_{a}[/tex] of carboxylic acid lies in the range of 1.92 - 4.76

[tex]pK_{a}[/tex] of phenol is 9.95

In sodium bicarbonate, [tex]HCO_{3}^{-}[/tex] acts as a strong base because it is derived from weak conjugate acid [tex]H_{2}CO_{3}[/tex]

Now, clearly, carboxylic acid will be preferably gives acid-base reaction with sodium bicarbonate to produce aqueous sodium carboxylate salt and phenol will remain as it is in a separate organic layer.

Unreacted phenol is then extracted with a suitable organic solvent by dissolving phenol in it.

Thus carboxylic acid and phenol can be separated by using aqueous sodium bicarbonate and a suitable organic solvent.