C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 2002
Extent and Intensity
2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
Teacher(s)
prof. RNDr. Jaroslav Jonas, CSc. (lecturer)
Guaranteed by
prof. RNDr. Jaroslav Jonas, CSc.
Chemistry Section – Faculty of Science
Prerequisites
Organic Chemistry I and II Physical 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
Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
Syllabus
  • 1.Pasteur and vant Hoff - two different ways to stereoochemistry. Symmetry-based and constitution-based approaches. Topological stereochemistry. 2. Inner coordinates of molecular structure, their changes through intramolecular dynamics and the corresponding energy landscape. Configuration and conformation. 3. Symmetry, asymmetry, dissymetry, and chirality. Molecular and local symmetry and point group classification thereof. 4. Local symmetry and stereogenicity. Prochirality and prostereogenicity. Symmetry of a dynamic molecular structure in relation to experimental time scale. 5. Isomerism and topicity with static molecular structures. Classification and methods of analysis. 6. Isomerism and topicity with dynamic molecular structures. Time scale of spectroscopic methods - especially NMR. 7. Absolute and relative configuration - methods for determination. 8. Racemic modifications, their separation into enantiomers. 9. Stereisomerism of acyclic and cyclic systems due to rotation around single bonds. 10. Stereoelectronic effects, especially the anomeric effect. 11. Stereoisomerism due to multiple bonds. 12.Stereodifferentiating reactions - classification and general considerations. 13. Stereodifferentiating reactions exemplified. 14. Stereochemistry of penta- and hexacoordinated compounds as compared to tetra-coordination. Stereochemical methodology - an overview.
Literature
  • Eliel E. L., Wilen S.H., Doyle M.P.: Basic Organic Stereochemistry, Wiley 2001, 704 pp., ISBN 0-471-37499-7
  • 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
  • ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
Assessment methods (in Czech)
A lecture interspersed with seminar - oral examination.
Language of instruction
English
Further comments (probably available only in Czech)
The course is taught annually.
The course is taught: every week.
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, 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, Autumn 2024.
  • Enrolment Statistics (Autumn 2002, recent)
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