C5510 Stereochemistry of Organic Compounds-seminar

Faculty of Science
Autumn 2022
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).
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 19:00–19:50 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
there are 15 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.
Learning outcomes
Student will be able to identify problems related to three-dimensional structure of organic compounds and use the knowledge obtained I the course fro solution of model exercises related to symmetry, chirality, identification, analysis and separation of isomers. He/she will be able to solve problems of stereoselective reaction and asymmetric synthesis.
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
Seminar. Class discussion of selected problems practising and extending the course objectives.
Assessment methods
Seminar with credit.
Language of instruction
Czech
Further Comments
The course is taught annually.
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 2023, Autumn 2024.
  • Enrolment Statistics (Autumn 2022, recent)
  • Permalink: https://is.muni.cz/course/sci/autumn2022/C5510