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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > July  >
In the Laboratory
The Microscale Laboratory
Evaluating Mechanisms of Dihydroxylation by Thin-Layer Chromatography
A Microscale Experiment for Organic Chemistry
Benjamin T. Burlingham and Joseph C. Rettig
Department of Chemistry, Mount Union College, Alliance, OH 44601
Cover
July 2008
Vol. 85 No. 7
p. 959

Abstract
A microscale experiment is presented in which cyclohexene is dihydroxylated under three sets of conditions: epoxidation–hydrolysis, permanganate oxidation, and the Woodward dihydroxylation. The products of the reactions are determined by the use of thin-layer chromatography. Teams of students are presented with proposed mechanisms for each dihydroxylation and are asked to evaluate them in light of data collected during the experiment. Both the timing of the lab in relation to the classroom curriculum and alternative applications of the lab are discussed.
Supplement
Student handouts including prelab and discussion questions; Instructor notes
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Citation
Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ. 2008, 85, 959.
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Keywords
Addition Reactions; Alkenes; Diastereomers; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; Mechanisms of Reactions; Microscale Lab; Organic Chemistry; Second-Year Undergraduate; Stereochemistry; Synthesis; Thin Layer Chromatography
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History
Created:
Last Updated:
5/27/2008
6/4/2008
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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