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Lab Report Williamson Ether Synthesis Of Phenacetin

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Experiment 6A: Williamson Ether Synthesis of Phenacetin This lab synthesized the organic compound phenacetin by performing a Williamson Ether Synthesis on acetaminophen. In this reaction acetaminophen’s hydroxyl hydrogen is substituted for an ethyl group to make phenacetin. An alcohol is being turned into an ester; where, the hydrogen of the hydroxyl group is removed by a carbonate anion and the remaining phenoxide anion backside attacks an ethyl iodine to obtain an ethyl group. If the reaction is successful the melting point should be around 134˙C and the IR spectrum should not have a peak around 3400 cm-1 (hydroxyl bond). To begin the experiment methyl ethyl ketone (solvent) is added to a vial containing the reagents of the reaction: acetaminophen, ethyl iodine, and potassium carbonate. This vial was …show more content…

Since, the extraction is on a microscale the aqueous layer is discarded by using a Pasteur pipette (DCM is denser than water so the aqueous layer is on the top). The organic layer contains the phenacetin (nonpolar) and the aqueous phase contains any remaining acetaminophen (polar). The DCM in the organic layer is then boiled off to reveal the crude product and then the crude product is weighed. The crude product came out to weigh 169 mg compared to the expected 177.79 mg, giving a percent yield of 95.1%. This crude product was then recrystallized to obtain a purer product. The crude product is dissolved in a minimal amount of boiling water (around 4 mL) and then slowly cooled to induce crystallization. After crystals formed (in ice bath) they were vacuum filtered and washed twice with 1 mL of cold deionized water and set to dry. The pure crystals weighed to be 70 mg, giving a percent yield of 39.4%. The dramatic change of product amount from crude to pure was most likely due to procedural error or the fact impurities were present in the

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