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Chapter 25: PROBLEM 25.18 (page 1016)

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

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Separation of the amine compound  

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.
02

Explanation

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

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