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How would you separate a mixuture containing 50% Benzoic Acid, 40% Benzoin, and

ID: 1002996 • Letter: H

Question

How would you separate a mixuture containing 50% Benzoic Acid, 40% Benzoin, and 10% 1,4-dibromobenzene with the following reagents available for use: 1 M NaOH, 1 M HCl, 6 M HCl, 1 M NaHCO3, saturated sodium chloride, diethyl ether, 95% ethanol, methanol, isopropyl alcohol, acetone, hexane, toulene, methylene chloride, and granular anhydrous sodium sulfate? I need detailed instructions with why using a particular reagent would work to separate out the components. The other answers for this question available on here and yahoo were not sufficent. Thank you in advance for the help.

Explanation / Answer

Solution:

As the given compund is of aromatics which can be extracted by sequential method, dissolve 1,4-dibromobenzene and benzil in methylene chloride and wash with sodium hydroxide in this state benzil exists as benzoin in equilibrium, the enolate formed should be soluble in basic aqueous conditions. By this the given mixture can be separated the percentage of the components can be weighed at the ened of extraction process.

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