C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 2024
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).
In-person direct teaching
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
Wed 13:00–14:50 A08/309
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 / plans the course is directly associated with
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.
Learning outcomes
Student will understand concept of isomerism of chemical compounds;
will be able to work with concepts conformation, configuration, chirality and optical activity;
will be able to chose suitable methods for identification of stereoisomers, determination of their contents in mixtures, and their possible separation;
utilize symmetry for elucidation of heterotopicity of homomorphic ligands and faces;
recognize stereoselective reactions and explain reasons of their selectivity based on steric, stereoelectronic and further effects;
utilize basic chiroptic methods for analysis and identification of chiral compounds.
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). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
  • ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. 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
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 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023.
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