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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > January  >
In the Laboratory
Reaction of Morpholine with t-Butyl Acetoacetate: A Study in Kinetic vs Thermodynamic Control, Product Identification, and Molecular Modeling
A. Gilbert Cook and Pamela K. Kreeger
Department of Chemistry, Valparaiso University, Valparaiso, IN 46383
Cover
January 2000
Vol. 77 No. 1
p. 90
Abstract
The reaction of morpholine with t-butyl acetoacetate in a one-to-one molar ratio will produce the corresponding enaminoester under kinetic control conditions and the ketoamide under thermodynamic control conditions. Students can identify the reaction products using NMR, IR, and GC-MS, but certain pitfalls to be avoided in this identification are pointed out. Molecular modeling of each of the two possible products gives the same results as the laboratory experiment. The possible use of microwave radiation is discussed.
More Information
*  Citation
 Cook, A. Gilbert; Kreeger, Pamela K. J. Chem. Educ. 2000 77 90.
*  Keywords
 NMR Spectrometry; Mass Spectrometry; Computational Chemistry; Organic Chemistry; Organic Synthesis; Laboratory Instruction; Molecular Modeling / Dynamics
*  History
 Created:
Last Updated:		 December 9, 1999
April 15, 2005
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