4. In the past we used to use sodium hydroxide instead of sodium bicarbonate in

Question

4. In the past we used to use sodium hydroxide instead of sodium bicarbonate in this lab. Students frequently observed that their sodium hydroxide solution was colored due to hydrolysis of small quantities of acetaminophen by sodium hydroxide to form 4-aminophenol, which is Oxidized to a highly colored compound. Explain where the separation could allow traces of acetaminophen in the aspirin and caffeine solution. The solubility in CHC, is; acetaminophen, 0.0005; aspirin, 0.033; caffeine, 0.089 g/mL. IHCCH , NHz NaOH OH Acetaminophen 4-Aminophenol

Explanation / Answer

Acetaminophen due to its low solubility in CH2Cl2 can easily be separated from aspirin and caffeine.

To the mixture of the three compounds add minimal amount of CH2Cl2, acetaminophen remain insoluble and can be separated from aspirin and caffeine in solution. The aspirin and caffeine can now be easily separated by first an aqueous base tratement, separation and then followed by an acid tretment.

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