Identification of an Unknown Organic Compounds

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Introduction

One of the most important tasks that chemists are faced with is the separation and identification of compounds from mixtures. Gratifyingly, chemists have multiple tools in the quest to identify unknown organic compounds. Infrared spectroscopy is useful for determining functional groups that may exist in a molecule. NMR spectroscopy tells information about the connectivity of C-H bonds, as well as the numbers of and chemical environments of both carbon and hydrogen (as well as many other NMR active nuclei, such as fluorine and phosphorus). Mass spectrometry is also a very powerful tool. Weakly ionizing methods such as MALDI (matrix-assisted laser desorptive ionization) and ESI (electrospray ionization) give molecular ions (gives you the molecular weight of the molecule), while strongly ionizing methods such as EI (electron impact) and CI (chemical impact) generate significant fragmentation, which can be used to determine pieces that can fall off of the molecule in the mass spectrometer.

Background

After years of study, you have recently finished your graduate degree, and have just accepted a position at a small liberal arts college. You show up the first day and look into your new lab, and see that there are numerous unlabeled containers. The previous occupant has retired at the beginning of the summer, and is apparently somewhere in the middle of the Atlantic Ocean now, enjoying retirement (and coincidentally cannot be reached). You’re unsure whether or not any of the compounds are useful, but thankfully the department you’re in has a GC-MS, as well as NMR and IR spectrometers. Using these instruments, you’re confident that you can identify all three of these compounds. Although there are no labels, you know based on the previous professor’s research that the compounds are likely to be from one of the following classes of compounds: Alcohols and phenols, aldehydes and ketones, amines, or carboxylic acids, amides, and esters.

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