A project is described for the advanced organic laboratory, specifically for students about to embark on an undergraduate organic research experience. Participants worked independently at their own pace and ran their own NMR spectra. Emphasis for participants was placed on development of skills and being able to carry out procedures described in the journal literature. Benzyl azide and terminal alkynes were cyclized to form 1,4-disubstitued 1<i>H</i>-1,2,3-triazoles by four different synthetic methods by each participant. Participants compared the overall results and decided which method or methods worked best of the four different procedures tested. Overall efficiency of each of the methods was the main basis for comparison, which included factors of yield of pure product, quality of the products based upon NMR spectral data, time necessary for the experiment and ease of work-up and purification. <sup>19</sup>F NMR data will also be discussed for a comparable set of experiments using fluorinated starting materials.

NMR spectroscopy as a component of an advanced organic laboratory project

2019 Spring National Meeting

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