acetaminophen

acetaminophen - Vu La January 14, 2010 Chemistry 112L...

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Vu La January 14, 2010 Chemistry 112L Medical Chemistry: From Tylenol to a Banned Chemical - Prelab 1) 2) See Back 3) Extracting with MTBE allows you to isolate the synthesized phenacetin from the KI and KHCO3 formed in the reaction. This is because phenacetin is a neutral compound that will dissolve in MTBE and the other compounds are polar compounds which will stay dissolved in the butanone. Unreacted acetaminophen will also dissolve into the MTBE. 4) The addition of NaOH solution turns acetaminophen into a salt to be dissolved into the aqueous layer. Basically through an acid base reaction you transfer acetaminophen to the aqueous layer while phenacetin is left in the organic layer to be extracted. This is because phenols like acetaminophen are acidic and ethers like phenacetin are neutral and the strong base deprotonates and polarizes the phenol. The addition of NaCl is like a pre-drying step. NaCl reduces miscibility between layers reducing the amount of water present in the organic layer before drying. M.M.
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This note was uploaded on 05/26/2011 for the course CHEM 112L taught by Professor Palleros during the Winter '11 term at UCSC.

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acetaminophen - Vu La January 14, 2010 Chemistry 112L...

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