A student tried to perform the reaction outlined below, which is a base-catalyze
ID: 523779 • Letter: A
Question
A student tried to perform the reaction outlined below, which is a base-catalyzed ester hydrolysis, followed by pH adjustment to 2. The student tried to distill the resulting p- methylphenol, but did not observe any product in the distillate collected, even after prolonged heating. Explain why. Seeing as the distillation failed as a purification method, outline a work up reaction that could be used to separate the benzoic acid and the p-methylphenol. Your outline should contain specific information, and should also be based on encountered in this course. Please note that chromatography is not an option in this case, as the benzoic acid is too polar.Explanation / Answer
A) when the products were heated in acidic medium, they reacted among themselves and the reaction went in reverse direction in acidic medium to give back reactant ester.
B) to separate them, first add saturated solution of sodium bicarbonate till the solution becomes basic. After neutralization of the aqueous acid in the mixture, sodium bicarbonate will form salt with the relative stronger acid, that is benzoic acid. The phenol derivative will remain unaffected. Add organic solvent like diethyl ether in the mixture to dissolve the organic phenol derivative and extract it using separatory funnel. Extract it three times with diethyl ether to remove all the phenol derivative. Then in the aqueous layer, add strong acid like HCl, drop wise to neutralize the solution. Now use the organic solvent like diethyl ether to extract back the benzoic acid which has been neutralized back to it's organic form.
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