Question: Write out steps to show how each of the following pairs of compounds can be separated by an extraction procedure.

a.

and

b.

and

An amine can be separated from other organic compounds by converting it to a water-soluble ammonium salt by an acid-base reaction. In each case, the extraction procedure will employ the following steps:

• Dissolve the amine and either X or Y in CH₂Cl₂ .
• Add a solution of 10% HCl. The amine will be protonated and dissolved in the aqueous layer, while X or Y will remain in the organic layer as a neutral compound.
• Separate the layers.

a. The salts are soluble in water, and the non-polar compounds are insoluble in water.

The reaction is shown as follows.

Solubility of the products in the respective solvents

b. The tertiary amine forms a salt. The higher ether compounds are insoluble in water.

Solubility of the products in the respective solvents