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ERIC Number: EJ939014
Record Type: Journal
Publication Date: 2011-Jul
Pages: 3
Abstractor: As Provided
Reference Count: 20
ISSN: ISSN-0021-9584
Investigating the Mechanism of Heteroaromatic Decarboxylation Using Solvent Kinetic Isotope Effects and Eyring Transition-State Theory
Mundle, Scott O. C.; Opinska, Liliana Guevara; Kluger, Ronald; Dicks, Andrew P.
Journal of Chemical Education, v88 n7 p1004-1006 Jul 2011
An upper-level mechanistic organic experiment is outlined where undergraduates measure kinetic rate constants for decarboxylation of pyrrole-2-carboxylic acid by the initial-rates method. UV spectroscopy is used to monitor reactant disappearance in both hydrochloric acid and deuterium chloride at different temperatures. Individual data are pooled and utilized by the class to calculate solvent kinetic isotope effects and reaction activation parameters (the latter from Eyring plots). Students interpret experimental results and additional literature data to deduce likely operative decarboxylation mechanisms at varying acidities. (Contains 2 figures and 1 scheme.)
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:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A