Suppose you want to separate a mixture of the following compounds: salicylic acid, 4-ethylphenol, p-aminoacetophenone, and napthalene. Come up with a list of steps and chemicals needed to most efficiently isolate all four compounds as solids with the greatest purity possible. You do not need to write a formal procedure, but be sure to indicate steps needed clearly and in order.

The procedure you will use in this exercise exploits the difference in acidity and solubility just described.

(a) you will dissolve your unknown in ethyl acetate (an organic solvent). All of the possible compounds are soluble in ethyl acetate.

(b) you will extract with sodium bicarbonate to remove any carboxylic acid that is present.

(c) you will extract with sodium hydroxide to remove any phenol that is present.

(d) you will acidify both of the resulting aqueous solutions to cause any compounds that were extracted to precipitate.