A -78°C Sequential Michael Addition for the Organic Lab

Michael W. Tanis
Department of Chemistry, Eastern College, St. Davids, PA 19087
J. Chem. Educ., 1997, 74 (1), p 112
DOI: 10.1021/ed074p112
Publication Date (Web): January 1, 1997
History, Education, and Documentation

Abstract

Organic reactions that require very cold temperatures (-78 oC) are routinely carried out in the research laboratory, but rarely (if ever) have such reactions been a part of the teaching laboratory. This is an unfortunate shortcoming, because students are always interested in an experiment that involves dry ice! The novelty of using a dry ice/isopropanol bath provides welcome variety from the usual mix-and-heat experiments of the organic laboratory course. Reactions at cold temperatures probably have been avoided in the teaching lab for two reasons: (i) usually the reactions require highly reactive compounds that raise safety concerns; (ii) the additional equipment that would be required for cold-temperature manipulations is thought to be too costly and to require skills beyond those of undergraduate students. This paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Addition Reactions
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  • Received: August 03, 2009

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