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Chirality A series of chiral and achiral objects, the interaction of polarized light with organic molecules, the assignment of R- and S- configuration, Fisher projections, and a stereospecific reaction are demonstrated.
Organic : IDChiralAtoms (20 Variations) Identify the chiral carbon atom(s), if any, in the following structure. The carbon atoms have been numbered for easier identification.
Frank Westheimer's Early Demonstration of Enzymatic SpecificityAddison Ault Reviews one of the most significant accomplishments of one of the most respected chemists of the 20th centurya series of stereospecific enzymatic oxidation and reduction experiments that led chemists to recognize enantiotopic and diastereotopic relationships of atoms, or groups of atoms, within molecules. Ault, Addison. J. Chem. Educ.2008, 85, 1246.
Asymmetric Synthesis |
Bioorganic Chemistry |
Catalysis |
Chirality / Optical Activity |
Enantiomers |
Enzymes |
Isotopes |
Nucleophilic Substitution |
Oxidation / Reduction |
Stereochemistry
The Same and Not the Same: Chirality, Topicity, and Memory of ChiralityWolfgang H. Kramer and Axel G. Griesbeck Describes a simple molecular approach that aids students in learning stereochemical terms, definitions, and concepts, particularly when chemical structures are drawn in two dimensions. Kramer, Wolfgang H.; Griesbeck, Axel G. J. Chem. Educ.2008, 85, 701.
Chirality / Optical Activity |
Stereochemistry
Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active AminesDamian A. Allen, Anthony E. Tomaso, Jr., Owen P. Priest, David F. Hindson, and Jamie L. Hurlburt In this experiment, teams of students are given an optically-pure amine of known structure but unknown stereochemistry. Different teams derivatize samples of the amine with (R) and (S) conformations of Mosher's acid chloride. The resulting diastereomers are analyzed by NMR to determine the absolute configuration of the initial, unknown amine. Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L. J. Chem. Educ.2008, 85, 698.
Stereochemistry TutorialNicola Burrmann Master the concepts organic stereochemistry with this interactive tutorial. It includes definitions, different three dimensional representations, assigning priorities to stereocenters, and determining the stereochemical relationship between molecules. Each section is followed by a question set that tests knowledge and understanding.
Stereochemistry |
Chirality / Optical Activity
Properties of AlkanesEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Chirality / Optical Activity
Collection of Chiral Drug, Pesticide, and Fragrance Molecular ModelsWilliam F. Coleman The article by Mannschreck, Kiessewetter, and von Angerer on the differential interactions between enantiomers and biological receptors (1) is the source for this month's Featured Molecules. Included in the molecule collection are all of the molecules described in the paper. In many instances we have included structures of multiple optical isomers of the same molecule so that students can not only see the forms that are active, but those that are less active, inactive, or act in an undesirable manner. These molecules will serve as good practice in determining optical configurations, and will also introduce additional forms of isomerism that students may be less familiar with than they are with R and S. Since multiple enantiomers and diastereomers are provided, students may use these molecules, together with an appropriate computational package, to verify that enantiomers have the same energy while diastereomers do not. The tuberculosis drug ethambutol provides an interesting case as both nitrogen atoms are also chiral as well as the two chiral carbon atoms. A calculation on a given structure will include the effect of that nitrogen chirality, although nitrogen inversion is expected to be quite rapid in this molecule. The conformations for the ethambutol molecules that are included here consider all four chiral atoms and are of the form (CNNC). A reasonable computational exercise would be to find the transition state for nitrogen inversion and the barrier height for that process. The supplemental material that is included with the featured article (1) includes a number of molecules that we will add to the collection as time permits. The result, including enantiomers and diastereomers, will be well over 200 additional molecules. A notice will appear in the JCE Featured Molecules column when this new set of molecules is available in JCE Online.
