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An unknown mixture (dissolved in diethyl ether) contains only 2 of the following : benzoic acid,...

An unknown mixture (dissolved in diethyl ether) contains only 2 of the following : benzoic acid, phenol, aniline and napthalene. You use the acid-base extraction method and want to identify the 2 compounds in your original mixture.

1) To separate the organic acid you add NaOH and to separate the organic base you add HCl.In both cases these extractions are followed by extractions with water. Why do we add water? Why is this step important? (A clear explanation please).

2)When neutralizing the alkaline extractions we add HCl. The colour of the extractions changes from pink to orange. What does this indicate? Is there any reaction occuring? How can I tell from this reaction that the organic acid in the original mixture is phenol and not benzoic acid? (Answer should include terms like weak/strong, precipitation) What would I observe if my organic acid was benzoic acid? What do I observe in the case of phenol?

3)How do I tell if there is aniline in my original mixture after adding NaOH to neutralize the acidic extractions?

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