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Hetero Diels-Alder Reaction with Aqueous Glyoxylic Acid: An Experiment in Organic Synthesis and 2-D NMR Analysis for Advanced Undergraduate Students
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Abstract
As an application of the use of water as solvent in organic synthesis, a convenient synthesis of α-hydroxy-γ-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.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
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This article has been cited by 8 ACS Journal articles (5 most recent appear below).
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Thomas P. Clausen , Thomas K. Green and Benjamin SteinerJournal of Chemical Education2008 85 (5), 692In teaching organic chemistry laboratory at this university, we eliminated the use of "canned" experiments from textbooks. Instead, we present students with literature studies that form the basis of developing new unpublished experiments to answer ...
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- Received: August 03, 2009
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