C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 2018
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).
Teacher(s)
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
Timetable
Mon 17. 9. to Fri 14. 12. Wed 12:00–13:50 A8-309
Prerequisites
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 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.
Syllabus
  • 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.
Literature
  • 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
Lectures
Assessment methods
Oral exam follows a written test.
Language of instruction
Czech
Further Comments
Study Materials
The course is taught annually.
Listed among pre-requisites of other courses
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2019.
  • Enrolment Statistics (Autumn 2018, recent)
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