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  Home > JCE Print > Journal of Chemical Education > Issues > 1998  > October  >
In the Laboratory
Hetero Diels-Alder Reaction with Aqueous Glyoxylic Acid: An Experiment in Organic Synthesis and 2-D NMR Analysis for Advanced Undergraduate Students
Jacques Augé and Nadège Lubin-Germain
Department of Chemistry, University of Cergy-Pontoise, 95031 Cergy-Pontoise, France
Cover
October 1998
Vol. 75 No. 10
p. 1285
Abstract
As an application of the use of water as solvent in organic synthesis, a convenient synthesis of a-hydroxy-g-lactones from an aqueous solution of glyoxylic acid is described. The mechanism of the reaction leading to the lactones goes through cycloadducts which rearrange in situ. The NMR analysis of the diastereomeric lactones is particularly interesting; such an analysis illustrates the importance of modern techniques including 2-D NMR spectroscopy. Complete assignments of the signals are mentioned and NOESY spectra are enclosed. The full experiment is addressed to advanced undergraduate students who are trained in organic synthesis and NMR spectroscopy.
More Information
*  Citation
 Augé, Jacques; Lubin-Germain, Nadège. J. Chem. Educ. 1998 75 1285.
*  Keywords
 organic chem, synthesis, NMR spectrometry, aqueous solution chem, laboratory instruction
*  History
 Created:
Last Updated:		 June 21, 1999
June 24, 2005
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