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Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic Laboratory

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John J. Nash , Marnie A. Leininger and Kurt Keyes

Department of Chemistry, Purdue University, West Lafayette, IN 47907

J. Chem. Educ., 2008, 85 (4), p 552

DOI: 10.1021/ed085p552

Publication Date (Web): April 1, 2008

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Alkenes

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Analytical Pyrolysis−Chromatography: Something Old, Something New
Nathan W. Bower and Conor J. K. Blanchet
Journal of Chemical Education2010 87 (5), 467-469
- Analytical Pyrolysis−Chromatography: Something Old, Something New
  Nathan W. Bower and Conor J. K. Blanchet
  Journal of Chemical Education2010 87 (5), 467-469
  Despite a long history of use across multiple disciplines, analytical pyrolysis is rarely taught in undergraduate curricula. We briefly review some interesting applications and discuss the three types of analytical pyrolyzers available commercially. We ...
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