Undergraduate Laboratory Experiment To Determine Absolute Configuration Using Thin-Layer Chromatography

• Autores: Alexander J. Wagner, Shawn M. Miller, Steven Nguyen, Ga Young Lee, Scott D. Rychnovsky, Renee D. Link
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 91, Nº 5, 2014, págs. 716-721
• Idioma: inglés
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• Resumen

  • A new undergraduate organic chemistry laboratory experiment has been developed to determine the absolute configuration of enantioenriched secondary alcohols with the competing enantioselective conversion (CEC) method. The CEC method uses both enantiomers of a chiral kinetic resolution reagent in parallel reactions to identify the fast-reacting reagent and thus the configuration of the alcohol. Students working in pairs are given one of three enantioenriched secondary alcohols with an unknown absolute configuration. They assign the molecular structure using the corresponding 1H NMR spectrum and determine the absolute configuration via the CEC method. The parallel reactions are run at room temperature for 1 h using small quantities of solvent, substrate, and catalyst. Students use thin-layer chromatography (TLC) to analyze the parallel reactions and determine the fast reaction qualitatively. The free program ImageJ is used with a picture of the TLC plate to carry out a quantitative analysis of reaction conversion. Data collected in the spring 2013 laboratory course (n = 1036) show that 93.6% of students determined the absolute configuration of their unknown correctly with just a qualitative analysis of the TLC plate. This experiment provides a platform for discussions of stereochemistry, mechanism, kinetics, energy diagrams, and transition states.