Let’s say you have an organic compound with a pKa of 5. In an organic/aqueous system, you add a ...

The bottom organic layer

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One gram of a compound requires the following quantities of solvent to dissolve: 47 mL of water, 8.1 mL of chloroform, 370 mL of diethyl ether, or 86 mL of benzene. Calculate the solubility of the compound in these four solvents (as g/100 mL). Estimate the partition coefficient of the compound between chloroform and water, ethyl ether and water, and benzene and water. Which solvent would you choose to extract the compound from an aqueous solution?

The data is summarized in the table below. K is calculated from K = Corganic solvent/Cwater. Chloroform would be the solvent of choice to extract the compound from an aqueous solution because the partition coefficient for this pair of solvents is the highest.

Solvent Given g/100 mL K
Water 1 g/47 mL 2.1 -
Chloroform 1 g/8.1 mL 12.3 5.9
Diethyl ether 1 g/370 mL .27 .13
Benzene 1 g/86 mL 1.2 .57


Therefore , the answer is the bottom aqueous layer.

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