Chemiluminescence Demonstration Illustrating Principles of Ester Hydrolysis Reactions
submitted by: Andrew G. Hadd, David W. Lehmpuhl, Laura R. Kuck, and John W. Birks Department of Chemistry and Cooperative Institute for Research in Environmental Science (CIRES), University of Colorado, Boulder, CO 80309-0216
checked by: Galen P. Mell Division of Biological Sciences, University of Montana, Missoula, MT 59812-1002
Peroxyoxalate chemiluminescence, the most efficient nonenzymatic chemiluminescence reaction known, is used to demonstrate mechanistic features of analogous ester hydrolysis reactions. The effect of the leaving group pKa and a comparison between nucleophilic and general-base catalysis are demonstrated visually by the kinetics of the light-generating reaction. The demonstration is targeted for undergraduate organic chemistry students but is easily modified for a range of audiences.
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Citation
Hadd, Andrew G.; Lehmpuhl, David W.; Kuck, Laura R.; Birks, John W. J. Chem. Educ.1999 76 1237.
Keywords
Demonstrations; Organic Chemistry; Kinetics; Luminescence; Mechanisms; Excited States / Energy Transfer
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