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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > April  >
In the Laboratory
Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic Laboratory
John J. Nash, Marnie A. Leininger, and Kurt Keyes
Department of Chemistry, Purdue University, West Lafayette, IN 47907
Cover
April 2008
Vol. 85 No. 4
p. 552

Abstract
The aryl sulfonate ester, menthyl N-acetylsulfanilate, is synthesized from N-acetylsulfanilyl chloride and menthol in pyridine, then pyrolyzed (thermally decomposed) at reduced pressure. The volatile (elimination) products of the reaction are analyzed using gas chromatography, and the resulting product distribution is used to determine whether the thermal decomposition occurs via an E1 mechanism or an E2 mechanism.
Supplement
Student handouts; Instructor notes
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Citation
Nash, John J.; Leininger, Marnie A.; Keyes, Kurt . J. Chem. Educ. 2008, 85, 552.
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Keywords
Alkenes; Carbocations; Elimination Reactions; Gas Chromatography; Hands-On Learning / Manipulatives; Laboratory Instruction; Mechanisms of Reactions; Organic Chemistry; Problem Solving / Decision Making; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
2/26/2008
3/5/2008
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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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