Course: Stereochemistry

« Back
Course title Stereochemistry
Course code OCH/SCH
Organizational form of instruction Lecture + Seminar
Level of course Master
Year of study 3
Semester Winter and summer
Number of ECTS credits 4
Language of instruction Czech
Status of course Compulsory, Compulsory-optional, Optional
Form of instruction Face-to-face
Work placements This is not an internship
Recommended optional programme components None
  • Okorochenkov Sergii
  • Hlaváč Jan, prof. RNDr. Ph.D.
Course content
Attention is paid to optical and geometrical isomers, their properties, nomenclature, methods of resolution and separation with use of modern analytical methods, especially NMR spectroscopy. The lecture is also aimed on relationship of reactivity and conformation of organic compounds as well as to principles of stereo selective reactions. 1. Molecular geometry, bonding parameters - bond length, angle, dihedral angle, deformation of bonding angle, hydrogen bonds, rotation around the bond. Molecular symmetry and chirality - classification, distinguishing. 2. Stereoisomerisms and center of chirality - molecules with one chiral center, configuration nomenclature, molecules with more chiral centers. 3. Axial and planar chirality - principles, stereochemistry of allenes, spiranes, biphenyles, cyclophanes, helicity, nomenclature. 4. Topicity and prostereoisomerism - homotopicity, enanciotopicity, diastereotopicity, nomenclature, NMR spectra, chemical and biochemical transformations. 5: Racemization and methods of resolution , mechanism of racemization, asymmetric transformation and mutarotation, methods of separation, optical purity. 6. Distinguishing of configuration - absolute configuration, correlation methods, configuration and character of geometric isomers. 7. Conformation of acyclic compounds - molecular mechanical pinciples and conformation, Klyne-Prelog terminology of torsion angles, methods of conformation analyses, conformation around sp3-sp3, sp3-sp2 bonds and carbon-heteroatom bonds. Character of conformers . 8. Conformation of cyclic molecules - cyclohexane, mono, di- and polysubstituted cyclohexanes, cyclohexane ring with sp2 carbons. 9. Conformation of cyclic compounds - rings different from cyclohexane, heterocycles. 10. Conformation of condensed and bridged cyclic systems - preparation, stability, reactivity, character. 11. Molecular dissymmetry and chiroptopic character - polarized light and its parameters, ORD and CD - characterization and application. 12. Dynamic stereochemistry - conformation and reactivity of rigid and mobile diastereoisomers, quantitative correlation between conformation and reactivity. 13. Conformation and reactivity of cyclic compounds, atropoisomers. 14. Stereo selective reactions - principles, classification, terminology, stereo selective reactions of acyclic and cyclic compounds, enantio selective reactions. Seminar is focused on training of the theoretical results with use of concrete examples. Students will create their space orientation of molecules and relationship between steroisomers. They will train to compare analytical data with studied structure. They will also train the nomenclature of stereoisomers and prostereoisomers.

Learning activities and teaching methods
Learning outcomes
The subject is focused on all aspects of space isomerism, space relationship in molecules and relationship between structure and physico-chemical properties.
Explain main spatial parameters and their relations to the properties of organic molecules

Assessment methods and criteria
Oral exam, Written exam

The subject is terminated by credit and examination. Credit is a writing test and is given in obtaining 60% points from each of the two exams during the semester. Written tests are focused on examples of current taught area. When failure is possible to obtain credit at an alternative date the successful fulfillment exam focusing on examples from around the discussed of subject matter and 60%. Enrollment for the examination is conditional on the successful acquisition of credit. During the examination, students show adequate theoretical knowledge from all of lectured areas.
Recommended literature
  • Eliel E.L.: Stereochemie uhlíkatých sloučenin, Academia Praha 1970. Potapov V.M.: Stereochemie, SNTL 1986..

Study plans that include the course
Faculty Study plan (Version) Branch of study Category Recommended year of study Recommended semester
Faculty of Science Chemistry (1) Chemistry courses 3 Summer
Faculty of Science Analytical Chemistry (2015) Chemistry courses - Summer
Faculty of Science Organic Chemistry (2016) Chemistry courses 1 Winter
Faculty of Science Biochemistry (1) Chemistry courses 3 Summer
Faculty of Science Biotechnology and Gene Engineering (1) Chemistry courses 3 Summer
Faculty of Science Bioinformatics (1) Informatics courses 2 Winter