SC CHEM 333 - Williamson Ether Synthesis Post-lab (3 pages)

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Williamson Ether Synthesis Post-lab



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Chemistry 333L 03M Post lab Williamson Ether Synthesis By Cameron Kahn TA James Collie 19 November 2013 Observations After mixing the initial solution comprised of 1 05g 2 naphthol 2 5mL ethanol 1mL of 6M NaOH and 1mL of 1 iodopropane the solution was brown in color before reflux As the solution was heat the solution became cloudier during the middle of the 40 minute reflux period Over the last 15 minutes of the reflux period the solution became clearer Once reflux was completed the solution left a ring of solid around the inside of the 25mL round bottom flask The layer of solid was noted to be somewhat tan in color The solution then went into a 50mL beaker containing 10mL of ice cold water and added ice small amount In the beaker the solution separated into two distinct layers one layer was a dark brown while the other was a lighter tan From there the entire contents of the 50mL beaker were then poured to the separatory funnel where 12mL of diethyl ether was added After swirling the mixture two layers formed The top organic layer was a dark brown color while the bottom aqueous layer was a light tan After removing the aqueous layer and boiling off the ether 3mL of 95 ethanol was added to the remaining milliliters of solution This step yielded a clear slightly colored solution After more than 10 minutes of the solution being introduced to the ice bath little to no crystals formed The melting point observed was 37oC Results Using a revised version of the intended Williamson Ether Synthesis as denoted in the lab manual the results were different The final product was 2 propoxynaphthalene After crystallization the measured mass of the filter paper and the product was 1 004g Subtracting the initial mass of the filter paper 0 182g from the total mass of the product with the filter paper gives the mass of the product The mass of the product was measured to be 0 822g Since we deviated from the lab manual the theoretical product yield cannot be calculated since the product



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