In this lab, butyl naphthyl ether was synthesized from 2-naphthol in the presence of sodium hydroxide, ethanol, and a butyl iodide using a Williamson Ether Synthesis reaction. The melting point of the resulting product was determined to be a range of 30℃-32℃, which is slightly below the literature value range (33℃-35℃). The relative proximity between the experimental melting point and the literature melting point range suggests that the product is fairly pure. Since there is a 1:1 ratio between the moles of 2-naphthol and butyl naphthyl ether, the theoretical yield of the reaction is 0.278 g, however the mass of the product was found to be 0.05 g, giving a percent yield of 18%. The low yield can be attributed to the loss of product through filtration. In future experiments, this mass loss could be avoided by using a different compound to cool the product without causing an overflow of liquid in the funnel during filtration that occurred when ice was used. Thin layer chromatography was used to further assess the purity and polarity of the product. The first solvent used consisted of a 95:5 mixture of hexanes:ethyl acetate. However this resulted in an uneven separation, presumably because of the high amount of the nonpolar hexanes compared to the polar ethyl acetate. On the other hand, a TLC test using a 95:5 mixture of ethyl acetate:hexanes resulted in an excessive amount of separation due to the high polarity of the solvent. Thus, it was a mixture of 90:10 hexanes:ethyl acetate mixture that provided the best separation. The presence of only one spot in the product column of the TLC plate indicated that the product is pure and consisted of only one component. However, this does not entirely confirm the purity of the product, as a single spot could be comprised of both the desired product and a second component of similar polarity. The product spot experienced a considerable amount of separation(Rf = 0.85) which was expected as butyl naphthyl ether is a relatively nonpolar compound and should show separation. 2-naphthol is a polar compound however, and thus should not experience much separation which was evident in the starting material spot and the co-spot (Rf = 0.17). As such, the results of the TLC analysis suggested that the product was indeed butyl naphthyl ether.
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