Draft 4

In this lab, an Sn2 reaction took place with 2-naphthyl as the nucleophile which displaced the iodide to form butyl naphthyl ether and sodium iodide. The percent yield I obtained from this experiment was 13.6%. The percent yield is relatively low. The first reason my products yield was low was because the melting point was very low, I noticed that as I was weighing the product some of the product melted on the filter paper. I could have avoided the loss of product this way by being more careful when handling the solid product and making sure no heat was applied to it. Also the addition of NaOH before refluxing is important so the product is properly deprotonated so that the product does not become oil when recrystallizing. If the product is oil instead of crystals then the product would go through the filtration. The melting point obtained was 31- 33⁰C. Compared to the melting point of butyl naphthyl ether which is 33-35^oC, the product produced in this lab was close in range to the one given to us. Therefore, my product is mostly pure although the discrepancies between the temperature given to us and the one obtained in the experiment can be explained the presence of possible impurities that are left in the product.