Chemical Education Today
Cautionary Comments I’m concerned about a safety factor in the paper, “A Solvent-Free Oxidation of Alcohols in an Organic Laboratory” (1). In my estimation, it is not a good idea to conduct a “nosolvent” reaction “…until the flask becomes warm”. As described, the experiment may never be a problem, but I can envision two scenarios where problems might occur: (i) The process is applied to a more reactive alcohol or (ii) there is unauthorized “scale up”. Literature Cited 1. Esteb, J. J.; Schelle, W.; Wilson, A. M. J. Chem. Educ. 2003, 80, 907. R. G. Landolt Department of Chemistry Texas Wesleyan University Fort Worth, TX 76105
[email protected] The authors reply:
Literature Cited
R. G. Landolt voices safety concerns over two possible scenarios in which a problem may occur with our procedure. Scenario 1 is the situation in which a more reactive alcohol is used, and Scenario 2 involves unauthorized “scale up”. Whenever changes are made to any procedure, one runs the risk of associated difficulties due to that change. We never intended our procedure to encompass the oxidation of all
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alcohols. As was demonstrated by Shaabani and Lee (1) in their original research paper from which this lab was devised, a variety of reaction conditions were necessary depending on the reactivity of the reagent used. We never claimed that our procedure would work as written for any alcohol other than the three that we have included. Furthermore, our only intention was to provide an alternative oxidation lab that cut back on waste and was more environmentally friendly than many of those that are currently available. We purposely chose three fairly representative alcohols (a straight-chain alcohol, a cyclic alcohol, and an alcohol containing aryl substituents) so that modification of the procedure should not be necessary. As for unauthorized scale up, the procedure as written may use either macroscale or microscale glassware and should therefore work in any undergraduate organic lab, thus eliminating the need for any modification. If anyone were to attempt any modifications to this reaction for research purposes, our hope is that they would consult the original reference which details the chemical oxidation of many species including alcohols, diols, thiols, and sulfides, and the inherent dangers involved with each of those reactions.
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1. Shaabani, A.; Lee, D. G. Tetrahedron Lett. 2001, 42, 5833. John J. Esteb and Anne M. Wilson Department of Chemistry Butler University Indianapolis, IN 46208
[email protected] Vol. 81 No. 5 May 2004
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Journal of Chemical Education
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