PřF:C5500 Stereochemistry of Org. Comp. - Course Information
C5500 Stereochemistry of Organic CompoundsFaculty of Science
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry - Chemistry Section - Faculty of Science
Supplier department: Department of Chemistry - Chemistry Section - Faculty of Science
- Mon 17. 9. to Fri 14. 12. Wed 12:00–13:50 A08/309
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry.
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001. xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993. xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002. 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest L. Stereochemie uhlíkatých sloučenin : Stereochemistry of carbon compounds (Orig.). Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970. 541 s. info
- Teaching methods
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Further Comments
- Study Materials
The course is taught annually.
- Listed among pre-requisites of other courses