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For a Diels-Alder Reaction laboratory experiment for Organich Chemistry class. If the hydrolysis to the diacid...

For a Diels-Alder Reaction laboratory experiment for Organich Chemistry class. If the hydrolysis to the diacid is not complete, how could you seperate the desired diacid from the hydrolyzed anhydride by extraction?

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The diacid can be made to react with a strong base inorder to convert it to the ionic form i.e the dicarboxylate ion which is soluble in water. Now you have two layers, one is an aqueous layer containing the dicarboxylate ion the other an organic layer with the unreacted anhydride. The aqueous layer can be separated using a funnel and the contents can be made to react with a strong acid like HCl. The dicarboxylate ion will react with HCl forming the dicarbxylic acid which being insoluble in aqueous medium will then precipitate out and can be filtered.

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