You have been given a mixture of benzoic acid, phenol, aniline, and methoxybenze

Question

You have been given a mixture of benzoic acid, phenol, aniline, and methoxybenzene in dichloromethane. How would you extract the benzoic acid? After accomplishing the goal of extracting the benzoic acid, how would you extract the phenol? After accomplishing the goal of extracting the benzoic acid and the phenol, how would you extract the aniline?

The choices are NaOH, HCl, NaHCO3, and chloroform are the choices. Would it be for benzoic acid--NaHCO3, for the phenol-would it be NaOH, and for the aniline--would it be NaOH?

Thanks!

Explanation / Answer

For benzoic acid, NaHCO3 is the choice because benzoic acid is the most acidic of all.

In the next step ( and not in the first), use NaOH to extract out phenol.

For aniline, its HCl since aniline is the most basic of all.

Separate the remaining by boiling off the mixture.

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