CHED 339 |
| The Cannizzaro reaction is a well-known oxidation-reduction reaction discovered 150 years ago. It involves two aldehyde molecules, one reduced to an alcohol and the second oxidized to a carboxylic acid. The currently accepted mechanism involves the intermolecular transfer of a hydride ion, which is a strongly basic, unlikely leaving group. Although the accepted mechanism is consistent with the existing evidence for the reaction, it is not consistent with normal organic chemistry, where intermolecular hydride transfer from a carbon is not well established. While studying this reaction, we used methoxide ion as a base in place of hydroxide ion. Products resulted that could not be produced by the accepted mechanism. Our new mechanism, involving a pericyclic reaction, is consistent with NMR and other experimental results, and does not involve the unfavorable intermolecular hydride transfer. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Chemical Education |