Chemistry 333L-03MPost-labWilliamson Ether SynthesisBy: Cameron KahnTA: James Collie19 November 2013Observations: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 solutionwas 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 we actually got (2-propoxynaphthalene) is different from the theoretical product denoted in the lab manual. Insufficient information was given to us in order to calculate the theoretical yield of 2-propoxynaphthalene and therefore a percent yield cannot be calculated. The actual melting point was 37°C while the theoretical melting point was 41°C. Comparing the two melting points, a 10.81% difference was calculated.Calculations:Final product:Total mass (filter paper + product) – mass of filter paper = Final product1.004g - 0.182g = 0.822gMelting point percent difference (oC):Theoretical melting point−actual melting pointactual melting pointx10041−3737x100= 10.81%2 | P a g eConclusion:Due to time constraints, we did an abbreviated Williamson Ether Synthesis. Using the revised procedures, we still performed a version of Williamson Ether Synthesis by synthesizing 2-propoxynaphthalene from the mixture of 1.05g 2-naphthol, 2.5mL ethanol, 1mL of 6M NaOH, and 1mL of 1-iodopropane. The 6M NaOH was the strong base. Between the processes of heating the solution and adding ether to separate out the organic product, we were able to obtain 0.822g of product. No IR-analysis was done on our sample. A 10.81% difference of melting points were observed and could be explained due to possible impurities such as chemical residues still left on the 25mL round bottom flask or the 50mL beaker from previous labs. Also due to not boiling off all the ether, some ether still remained in the final product. Because ether was still present in the product, this would explain why the crystallization of the product did not happen once the solution began to cool in the ice bath. All these occurrences were sources of error during the experiment. Apart from sources of error, the learning outcome from the lab showed the importance of Williamson Ether Synthesis. In general, Williamson Ether Synthesis isa Sn2 reaction of an alkyl halide reacts with an organic oxide anion to form a new carbon oxide bond (Handy). To produce many kinds of pharmaceuticals, the process of synthesis is needed in order to create a product that compare to the natural product. If we were to have done the procedures set on in the lab manual, one would synthesize Guaiacol through Williamson Ether Synthesis. This product compares to the natural product, Guaifenesin which is used in Mucinex®. Williamson Ether Synthesis is one of many synthesis processes and help chemists create pharmaceuticals including generic medicines.IR-analysis:Due to the absence of the TA to work the IR-spectroscopy machine, no group in lab was able to obtain an IR-graph of their sample to analyze. The IR results should show peaks between 1600cm-1 and 1475cm-1 to indicate the two aromatic benzene rings present in the product composition. Also sp2 hybridized carbons would be evident and peak at 3100cm-1 while sp3 hybridized carbons would be evident and peak at 2950cm-1 as well. Lastly, due to the presence ofether as an impurity, a peak at around 1150cm-1 should be seen.References:1. Ali, George Handy and Salman. Chemistry 333 & 334 laboratory Manual Experiemnts inOrganic Chemistry Fall 2012 - 2013. Montgomery, Al: QDE Press, Fall 2012.2. "2-Propoxynaphthalene." ChemSpider. N.p., n.d. Web. 18 Nov. 20133 | P a g