6.7. Molecules Containing Chiral Centers as Reactants or Products
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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 Aromaticity of Pericyclic Reaction Transition StatesHenry S. Rzepa Presents an approach that combines two fundamental concepts in organic chemistry, chirality and aromaticity, into a simple rule for stating selection rules for pericyclic reactions in terms of achiral Hckel-aromatic and chiral Mbius-aromatic transition states. Rzepa, Henry S. J. Chem. Educ.2007, 84, 1535.
Alkanes / Cycloalkanes |
Alkenes |
Aromatic Compounds |
Mechanisms of Reactions |
Stereochemistry
Iodolactonization of 4-Pentenoic Acid R. David Crouch, Alexander Tucker-Schwartz, and Kathryn Barker Describes an experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization. Crouch, R. David; Tucker-Schwartz, Alexander; Barker, Kathryn. J. Chem. Educ.2006, 83, 921.
Alkenes |
Carboxylic Acids |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactions |
Synthesis
The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors LaboratoryChristopher J. Nichols and Melissa R. Taylor A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column. Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ.2005, 82, 105.
