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Question

Consider the following pair of compounds:

Structures of compounds A and B, both phenols, illustrating their hydroxyl groups.

Compounds A and B are both sparingly soluble water. In dilute potassium hydroxide solution, compound B is very soluble but compound A is still sparingly soluble. Show how you can exploit this difference in solubility to separate these two compounds from a mixture.

Accepted Answer

1. Add dilute KOH solution and ether to the mixture.
2. The ether layer will contain A and B will dissolve in the dilute KOH solution.
3. Separate the layers and evaporate the ether layer to get A in pure form.
4. Acidify the aqueous layer with dilute HCl solution and extract again with ether.
5. Evaporate the ether layer to get B in pure form.

Answer

1. Add dilute KOH solution and ether to the mixture.
2. The ether layer will contain A and B will dissolve in the dilute KOH solution.
3. Separate the layers and evaporate the ether layer to get A in pure form.
4. Extract the aqueous layer with ethyl acetate.
5. Evaporate the ethyl acetate layer to get B in pure form.

Answer

1. Add dilute KOH solution and ether to the mixture.
2. The ether layer will contain B and A will dissolve in the dilute KOH solution.
3. Separate the layers and evaporate the ether layer to get B in pure form.
4. Acidify the aqueous layer with dilute HCl solution and extract again with ether.
5. Evaporate the ether layer to get A in pure form.

Answer

These compounds cannot be separated easily.

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