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The Discovery-Oriented Approach to Organic Chemistry. 2. Selectivity in Alcohol Oxidation. An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories
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Abstract
We have developed a simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine. 1H NMR analysis of the product mixture allows the student to determine the selectivity exhibited by the reagent.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Problem Solving / Decision MakingKeywords (Subject):
NMR SpectroscopyCiting Articles
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This article has been cited by 14 ACS Journal articles (5 most recent appear below).
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Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions
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Kendrew K. W. Mak , Y. M. Lai and Yuk-Hong SiuJournal of Chemical Education2006 83 (7), 1058This article describes a discovery-oriented experiment for demonstrating the selectivity of two epoxidation reactions. Peroxy acids and alkaline H2O2 are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich ...
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- Received: August 03, 2009
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