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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.
Evaluating Mechanisms of Dihydroxylation by Thin-Layer ChromatographyBenjamin T. Burlingham and Joseph C. Rettig Presents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected. Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ.2008, 85, 959.
Addition Reactions |
Alkenes |
Diastereomers |
Mechanisms of Reactions |
Microscale Lab |
Stereochemistry |
Synthesis |
Thin Layer Chromatography
Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-MethylstyreneBrad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. Murphy In the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition. Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ.2008, 85, 102.
Addition Reactions |
Alcohols |
Alkenes |
Constitutional Isomers |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis
Polar Addition to C=C Group: Why Is Anti-Markovnikov Hydroboration–Oxidation of Alkenes Not "Anti-"?Predrag-Peter Ilich, Lucas S. Rickertsen, and Erienne Becker The authors redefine Markovnikov or anti-Markovnikov regioselectivity and propose that the teaching of organic chemistry should be based on robust and portable concepts such as energy difference and atomic charge rather than historical labels. Ilich, Predrag-Peter; Rickertsen, Lucas S.; Becker, Erienne. J. Chem. Educ.2006, 83, 1681.
