SC CHEM 333 - Williamson Ether Synthesis Pre-Lab (5 pages)

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Williamson Ether Synthesis Pre-Lab



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Experiment 9 Williamson Ether Synthesis Pre Lab By Cameron Kahn 14 November 2013 TA James Collie Objectives In this lab one will learn Williamson Ether Synthesis He she will start with guaiacol and 3chloro 1 2 propanediol and using Williamson Ether Synthesis will end up with 3 2methoxyphenyloxy 1 2 propanediol as the product Simultaneously one will extract the natural product from Mucinex and then compare both product s melting point and IR analysis Intro In a Williamson Ether Synthesis the alkoxide functions as the nucleophile and attacks the electrophilic C of the alkyl halide displacing the bromide and creating the new C O bond Synthesis of Ethers The mechanism by which a Williamson Ether Synthesis works is by a bimolecular nucleophilic substitution otherwise known as a Sn2 reaction Primary alkyl halides are preferred in this reaction due to steric hindrance First discovered in nature Guiafensin has been used for many years including the use by Native Americans as a remedy The use of Guiafensin today is used in cough medicines and due to the demand synthesis is needed to create volume for the masses In this experiment one will compare the tablet natural form versus the synthesized form in order to identify which one is more pure In this experiment the use of acetonitrile as the solvent is needed for the reaction to undergo Sn2 Unlike phenoxide Acetonitrile is polar aprotic therefore eliminating any acid base chemistry that could occur Acetonitrile will not degrade any of the reagents before their used and has a boiling point of 82oC Handy The properties of Acetonitrile works well for a Sn2 reaction to occur In a Williamson Ether Synthesis a phase transfer catalyst is used however for our experiment the use of a catalyst will not be used In a typical Williamson Ether Synthesis the reaction is catalyzed with tetramethylammonium bromide This is important to note because a phase change causes an inorganic ion to move from aqueous solution to organic solution Without



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