In the organic chemistry course, unknown identification problems that use combinations of infrared, proton, and carbon nuclear magnetic resonance, and mass spectroscopy (or selections from these) are a good way for students to learn the power and the limitations of the individual spectroscopies and how they complement each other. However, consulting even multiple published sources, an instructor would be limited to the relatively small number of those problems suitable for his or her class. By using the vast number of spectra available on Internet databases, the instructor can create a different problem for each student but still have all problems be of comparable difficulty. In the teaching laboratory, the value of the personalized approach has long been recognized, as evidenced by the longevity of the unknown identification experiment. This classical exercise remains an ideal vehicle for showing the practical application of combined spectroscopic techniques.
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