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

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 invol...

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Bibliographic Details
Published inJournal of chemical education Vol. 74; no. 1; p. 112
Main Author Tanis, Michael W
Format Journal Article
LanguageEnglish
Published Easton Division of Chemical Education 01.01.1997
American Chemical Society
Subjects
Alkylation
Chemical reactions
Climate
Cold
College students
Dry ice
Experiments
Inhalants
Laboratories
Research Methodology
Science education
Students
Supervision
Teaching methods
Undergraduate Students
Second-Year Undergraduate
Hands-On Learning / Manipulatives
Addition Reactions
Organic Chemistry
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Summary: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.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed074p112