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The Discovery-Oriented Approach to Organic Chemistry. 5. Stereochemistry of E2 Elimination: Elimination of cis- and trans-2-Methylcyclohexyl Tosylate
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Abstract
The E2 elimination is one of the most important reactions in organic chemistry and is discussed in considerable detail in a sophomore organic course. We have developed a discovery-oriented lab that illustrates the stereochemistry of the E2 elimination reaction and is a good exercise in 1H NMR spectroscopy. The added element of discovery insures that student interest and enthusiasm are retained.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Inquiry-Based / Discovery LearningKeywords (Subject):
IR SpectroscopyCiting Articles
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This article has been cited by 11 ACS Journal articles (5 most recent appear below).
Using Group-Inquiry To Study Differing Reaction Conditions in the E2 Elimination of Cyclohexyl Halides
Robert D. LongJournal of Chemical Education2012 89 (5), 672-674Using Group-Inquiry To Study Differing Reaction Conditions in the E2 Elimination of Cyclohexyl Halides
Robert D. LongJournal of Chemical Education2012 89 (5), 672-674In this experiment, students individually conduct one of several variations of an E2 dehydrohalogenation reaction on a cyclohexyl halide substrate for 30 min, which is sufficient only for a partial reaction to occur. The variations examine reaction ...
Peer Mentoring in the General Chemistry and Organic Chemistry Laboratories. The Pinacol Rearrangement: An Exercise in NMR and IR Spectroscopy for General Chemistry and Organic Chemistry Laboratories
Caleb A. Arrington , Jameica B. Hill , Ramin Radfar , David M. Whisnant and Charles G. BassJournal of Chemical Education2008 85 (2), 288Peer Mentoring in the General Chemistry and Organic Chemistry Laboratories. The Pinacol Rearrangement: An Exercise in NMR and IR Spectroscopy for General Chemistry and Organic Chemistry Laboratories
Caleb A. Arrington , Jameica B. Hill , Ramin Radfar , David M. Whisnant and Charles G. BassJournal of Chemical Education2008 85 (2), 288This article describes a discovery experiment for general chemistry and organic chemistry labs. Although the pinacol rearrangement has been employed in undergraduate organic laboratories before, in this application organic chemistry students act as ...
Incorporating Guided-Inquiry Learning into the Organic Chemistry Laboratory
Allen M. Schoffstall , Barbara A. GaddisJournal of Chemical Education2007 84 (5), 848Incorporating Guided-Inquiry Learning into the Organic Chemistry Laboratory
Allen M. Schoffstall , Barbara A. GaddisJournal of Chemical Education2007 84 (5), 848Informed science educators who are responsible for undergraduate laboratory programs strive to improve the effectiveness of learning in the laboratory. Guided-inquiry learning in the laboratory is one reasonable alternative (among others described here) ...
The State of Organic Teaching Laboratories
Gail HorowitzJournal of Chemical Education2007 84 (2), 346The State of Organic Teaching Laboratories
Gail HorowitzJournal of Chemical Education2007 84 (2), 346This review explores the dramatic changes that have taken place in the organic chemistry laboratory course over the last two to three decades. The most significant changes have been in the areas of pedagogy and technology. Significant inroads have been ...
Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-Bromobenzoate
Eric J. Mahan and Mary Alice NadingJournal of Chemical Education2006 83 (11), 1652Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-Bromobenzoate
Eric J. Mahan and Mary Alice NadingJournal of Chemical Education2006 83 (11), 1652This experiment was designed to help students improve the critical thinking skills that are required to analyze and discuss the results of an organic chemistry experiment in an effective manner. The initial objective indicated in the prelab handout for ...
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- Received: August 03, 2009
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