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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > September  >
In the Classroom
"As Simple as Possible, but Not Simpler"—The Case of Dehydroascorbic Acid
Robert C. Kerber
Department of Chemistry, Stony Brook University, Long Island, NY 11794
Cover
September 2008
Vol. 85 No. 9
p. 1237
Abstract
Ascorbic acid (vitamin C) is an essential nutrient, whose metabolic roles depend on its function as a reducing agent. Textbooks routinely assign its oxidized form, dehydroascorbic acid, a tricarbonyl structure that is highly improbable in aqueous solution and inconsistent with its colorless appearance. The actual structures of the various forms of dehydroascorbic acid have been known for at least a quarter of a century so that the continued use of the oversimplified tricarbonyl structure is hard to excuse. The experimental results on studies of oxidized forms of ascorbic acid are summarized here, and a plea is entered for accurate descriptions of chemical structures in this and other cases, even at the cost of some simplicity. A group exercise based on dehydroascorbic acid, which we have used in second-semester organic chemistry, is included in the online material.
Supplement
Carbonyl addition reactions workshop exercise
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Citation
Kerber, Robert C. J. Chem. Educ. 2008, 85, 1237.
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Keywords
Biochemistry; Bioorganic Chemistry; Free Radicals; Misconceptions / Discrepant Events; Natural Products; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Vitamins
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History
Created:
Last Updated:
8/4/2008
8/4/2008
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