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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > June  >
In the Laboratory
The Baeyer–Villiger Oxidation with Trifluoroacetic Acid and Household Sodium Percarbonate
Richard A. Kjonaas and Anthony E. Clemons
Department of Chemistry, Indiana State University, Terre Haute, IN 47809
Cover
June 2008
Vol. 85 No. 6
p. 827
Abstract
A method for carrying out the Baeyer–Villiger oxidation of cyclopentanone to δ-valerolactone in a large-section introductory organic chemistry laboratory course is reported. The oxidizing agent is trifluoroperoxyacetic acid generated in situ from trifluoroacetic acid and household sodium percarbonate such as OxiClean, Oxi Magic, or Oxy-Boost. A class of 27 students can easily carry out the reaction and record a 1H NMR spectrum within a 3-hour lab period. Students typically report a 50% yield of isolated material.
Supplement
Student handouts; Instructor notes; 1H NMR spectra; A table showing the suitability of ten different household sodium percarbonate products
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Contents
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JCE2008p0827W.zip
JCE2008p0827W.doc (Microsoft Word)
More Information
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Citation
Kjonaas, Richard A.; Clemons, Anthony E. J. Chem. Educ. 2008, 85, 827.
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Keywords
Aldehydes / Ketones; Esters; Hands-On Learning / Manipulatives; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Oxidation / Reduction; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
5/5/2008
5/7/2008
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