PřF:C5510 Stereochem. of Org. Comp.-sem. - Course Information
C5510 Stereochemistry of Organic Compounds-seminarFaculty of Science
- Extent and Intensity
- 0/1/0. 1 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: z (credit). Other types of completion: zk (examination).
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, 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 14:00–14:50 A8-309
- 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 the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objective of the seminar is to discuss and analyze the topics of the lecture Stereochemistry of organic compounds on some ilustrative and practical examples following the syllabus of the lecture.
- 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). 1. vyd. 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
- Seminar. Class discussion of selected problems practising and extending the course objectives.
- Assessment methods
- Seminar with credit.
- Language of instruction
- Further Comments
- The course is taught annually.