9.11 Stereochemistry of Reactions: Addition of H2O to a Chiral Alkene
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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.
Borohydride Reduction of EstroneAnimesh Aditya, David E. Nichols, and G. Marc Loudon This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity using chiral hindered ketones that undergo facile reduction with sodium borohydride. The resulting diastereomeric estradiols can be analyzed and differentiated by thin-layer chromatography and melting point. Aditya, Animesh; Nichols, David E.; Loudon, G. Marc. J. Chem. Educ.2008, 85, 1535.
Aldehydes / Ketones |
Diastereomers |
IR Spectroscopy |
Microscale Lab |
Stereochemistry |
Steroids |
Thin Layer Chromatography
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
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.
Orbital Descriptions of Multiple BondsEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Diastereomers
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
Mage; A Tool for Developing Interactive Instructional GraphicsStephen F. Pavkovic Mage is a graphics program especially well suited for visualizing three-dimensional structures of proteins and other macromolecules. It is an important tool for biochemists and finds many applications in biochemistry courses. We utilize Mage to create interactive instructional graphics of potential use in a wider range of undergraduate chemistry courses, and present some of those applications here.
