Describe exactly how you would go about separating a mixture of the three water-insoluble liquids, aniline (b.p. 184 °C), n-butylbenzene (b.p. 183 °C) and n-valeric acid (b.p. 187 °C), recovering each compound pure and in essentially quantitative yield.
This is a question from Organic Chemistry by Morrison and Boyd. My problem is I know everything that is going to apply in this problem but I'm unable to execute the solution.
Things that I know:
1. Aniline is an amine attached to benzene group, n-butylbenzene is a benzene with a butyl group attached to one of its carbon atom, Valerie acid is pentatonic acid.
2. Aniline are polar and basic, Valeric acid are acidic, benzene is an electron withdrawing group.
3. Aniline are insoluble in water due to lack of hydrogen bonding.
How can solve this problem? Is my knowledge about the problem is insufficient? I have given this problem only to illustrate my problem with reasoning in chemistry, so please illustrate your answer by giving the solution of this problem or the way you find better.