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

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.

Journal of Chemical Education, 2000, 77, 90                       Full text (PDF)

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