Experiment 8

Experiment 8 - Vanessa Chew Ashleigh Ward Chem 3AL...

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Vanessa Chew Ashleigh Ward Chem 3AL November 13, 2010 Experiment 8: What do you take for pain? Discussion Acid-base chemistry was used to extract naproxen from its sodium salt. When sulfuric acid was added dropwise, it reacted with sodium naproxen to form pure naproxen, which is insoluble as water and thus appeared as a precipitate. Sodium hydrogen sulfate was also produced, which remained in aqueous solution: A good recrystallization solvent must not dissolve the compound at room temperature, but must dissolve it when heated, and allow the compound to drop out of solution when re-cooled. There was probably no pure solvent that had all these characteristics for naproxen. Hence, a mixed solvent system was necessary. Naproxen is extremely soluble in ethanol but insoluble in water. Combining these two miscible solvents provided a medium for naproxen to dissolve (due to the presence of ethanol) and recrystallize when cooled (due to the presence of water). Diethyl ether was not used as its boiling point, 35 ºC, is too low. Too much of the solvent
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This note was uploaded on 11/29/2010 for the course CHEM 3AL taught by Professor Li during the Fall '08 term at Berkeley.

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Experiment 8 - Vanessa Chew Ashleigh Ward Chem 3AL...

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