7.5. Stereoisomerism: Enantiomers and Diastereomers
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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
Percy Julian, Robert Robinson, and the Identity of EseretholeAddison Ault The Nova production Percy JulianForgotten Genius, which included the very public disagreement over the identity of "eserethole," the key intermediate for the synthesis of the alkaloid physostigmine, left three important chemical questions unanswered. Ault, Addison. J. Chem. Educ.2008, 85, 1524.
Constitutional Isomers |
Enantiomers |
Natural Products |
Stereochemistry |
Synthesis
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.
Orbital Descriptions of Multiple BondsEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Diastereomers
Mechanisms That Interchange Axial and Equatorial Atoms in Fluxional ProcessesMarion E. Cass, Henry S. Rzepa, King Kuok Hii The Berry pseudorotation is a classical mechanism for interchanging axial and equatorial ligands in molecules with trigonal bipyramidal geometry. Teaching this mechanism presents particular pedagogic problems due to both its dynamic and three dimensional character. The approach taken here illustrates these processes using interactive animations embedded in a Web page and overcomes many limitations of a printed page.
Computational Chemistry |
Molecular Properties / Structure |
Nonmetals |
Enantiomers |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Mechanics / Dynamics
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.
