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ERIC Number: EJ946468
Record Type: Journal
Publication Date: 2011-Oct
Pages: 2
Abstractor: As Provided
Reference Count: 15
ISBN: N/A
ISSN: ISSN-0021-9584
Substituent Effects on Keto-Enol Equilibria Using NMR Spectroscopy
Manbeck, Kimberly A.; Boaz, Nicholas C.; Bair, Nathaniel C.; Sanders, Allix M. S.; Marsh, Anderson L.
Journal of Chemical Education, v88 n10 p1444-1445 Oct 2011
In this extension to a classic physical chemistry experiment, students record the proton nuclear magnetic resonance spectra of the [beta]-diketones 2,4-pentanedione, 3-methyl-2,4-pentanedione, and 3-chloro-2,4-pentanedione to investigate the effect of substituents on keto-enol tautomerization equilibria. From the integrated intensities of keto and enol methyl proton peaks, students calculate the equilibrium constant for each 2,4-pentanedione. The students then use the effects of electron-donating and electron-withdrawing substituents to elucidate the nature of keto-enol equilibria. (Contains 2 tables.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A