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Competition Experiments as a Means of Evaluating Linear Free Energy Relationships. An Experiment for the Advanced Undergraduate Organic Chemistry Lab
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Abstract
A novel approach to exploring Hammett relationships in the undergraduate teaching lab is described. The use of competition experiments proved to be a reliable method for the construction of Hammett plots with good correlation. Reactions that were studied include the sodium borohydride reduction, methylmagnesium bromide addition, and oxime formation with para-substituted acetophenones. The composition of reaction mixtures was established by 1H NMR integrations. The use of competition experiments ensured consistency in the results, as relatively little control was required over the reaction conditions. Thus, this method provides great flexibility with regard to the compounds and reactions that may be studied.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Inquiry-Based / Discovery LearningKeywords (Subject):
KineticsCiting Articles
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This article has been cited by 8 ACS Journal articles (5 most recent appear below).
Hammett Parameter and Molecular-Modeling Correlations of Substituent Effects on Esterification Kinetics
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A Boron-Substituted Analogue of the Shvo Hydrogenation Catalyst: Catalytic Hydroboration of Aldehydes, Imines, and Ketones
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Probing the Rate-Determining Step of the Claisen-Schmidt Condensation by Competition Reactions
Kendrew K. W. Mak , Wing-Fat Chan , Ka-Ying Lung , Wai-Yee Lam , Weng-Cheong Ng and Siu-Fung LeeJournal of Chemical Education2007 84 (11), 1819Probing the Rate-Determining Step of the Claisen-Schmidt Condensation by Competition Reactions
Kendrew K. W. Mak , Wing-Fat Chan , Ka-Ying Lung , Wai-Yee Lam , Weng-Cheong Ng and Siu-Fung LeeJournal of Chemical Education2007 84 (11), 1819Competition experiments are a useful tool for preliminary study of the linear free energy relationship of organic reactions. This article describes a physical organic experiment for upper-level undergraduates to identify the rate-determining step of the ...
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- Received: August 03, 2009
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