In an effort to introduce gas chromatography-mass spectrometry (GC-MS) analysis into the organic chemistry II laboratory curriculum, undergraduate students in the upper-level Instrumental Analysis course developed two GC-MS methods to be implemented in two well-known organic chemistry experiments: the synthesis of 2-chloro-2-methylbutane via an acid-catalyzed S<sub>N</sub>1 reaction of 2-methyl-2-butanol and the nitration of methyl benzoate via electrophilic aromatic substitution reaction. The GC was equipped with an autosampler, a split injector, a HP-5MS column (30 m x 0.25 mm x 0.25 µm), and a helium mobile phase. The MS was equipped with an electron impact ionization source and a quadrupole mass analyzer. The analytes in the crude products of the synthesis of a tertiary alkyl halide and the nitration of methyl benzoate were baseline separated under isothermal conditions within 3 min and 7 min, respectively. The identity of individual analytes was confirmed via comparison of retention times and mass spectra of respective standards. The favorable speed of these separations allows either experiment to be completed in one or two three-hour lab periods, including synthesis and product identification by IR, NMR and GC-MS.

Introducing GC-MS analysis into undergraduate organic chemistry II laboratory curriculum

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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