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Diels-Alder Visualization Several computer animations of a Diels-Alder reaction that were created as an undergraduate student project are presented.
Addition Reactions |
Alkenes
Addition Reactions of Alkenes The Diels-Alder reaction, addition of oxygen to tetrakis(N, N-dimethylamino) ethylene, polymerization of ethylene, and addition of iodine to a-pinene are demonstrated. Molecular models of ethene are shown.
The Iodochlorination of Styrene: An Experiment That Makes a DifferenceR. Gary Amiet and Sylvia Urban This purpose of this laboratory exercise is to determine the various substitution and elimination products generated in the iodochlorination of styrene and their relative proportions through the application of mechanistic principles and a basic knowledge of GCMS and NMR. Amiet, R. Gary; Urban, Sylvia. J. Chem. Educ.2008, 85, 962.
Alkenes |
Constitutional Isomers |
Gas Chromatography |
Instrumental Methods |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Synthesis |
Student-Centered Learning
Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic LaboratoryJohn J. Nash, Marnie A. Leininger, and Kurt Keyes An aryl sulfonate ester is synthesized and then pyrolyzed at reduced pressure. The volatile products are analyzed using gas chromatography to determine whether the thermal decomposition occurs via an E1 or E2 mechanism. Nash, John J.; Leininger, Marnie A.; Keyes, Kurt . J. Chem. Educ.2008, 85, 552.
Alkenes |
Carbocations |
Elimination Reactions |
Gas Chromatography |
Mechanisms of Reactions |
Synthesis
Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a β-BromostyreneThomas A. Evans The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes. Evans, Thomas A. J. Chem. Educ.2006, 83, 1062.
