Water and diethyl ether are immiscible liquids. Charged compounds dissolve in wa

Question

Water and diethyl ether are immiscible liquids. Charged compounds dissolve in water and uncharged compounds dissolve in ether. Given that benzoic acid has a pKa of 4.8 and cyclohexylamine has a pKa of 10.7: a. What pH would you make the water layer in order to cause both compounds to dissolve in the water? b. What pH would you make the water layer in order to cause the acid to dissolve in the water layer and the amine to dissolve in the ether layer? c. What pH would you make the water layer in order to cause the acid to dissolve in the ether layer and the amine to dissolve in the water layer? d. How would you purify a mixture of benzoic acid, chlorobenzene, and cyclohexylamine? (pKa of chlorobenzene is 43)

Explanation / Answer

If the pH of the water layer is below 2.8 the amine will dissolve in the water layer and the carboxylic acid will dissolve in the ether layer.

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