| Course title | Stereochemistry |
|---|---|
| Course code | OCH/SCH |
| Organizational form of instruction | Lecture + Seminar |
| Level of course | Master |
| Year of study | 2 |
| Semester | Winter |
| 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 |
| Lecturer(s) |
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| Course content |
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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.
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| Learning activities and teaching methods |
| Lecture |
| Learning outcomes |
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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 |
| Prerequisites |
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unspecified
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| Assessment methods and criteria |
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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 |
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| Study plans that include the course |
| Faculty | Study plan (Version) | Category of Branch/Specialization | Recommended semester | |
|---|---|---|---|---|
| Faculty: Faculty of Science | Study plan (Version): Biotechnology and Genetic Engineering (2022) | Category: Chemistry courses | 3 | Recommended year of study:3, Recommended semester: Winter |
| Faculty: Faculty of Science | Study plan (Version): Chemistry (2019) | Category: Chemistry courses | 3 | Recommended year of study:3, Recommended semester: Winter |
| Faculty: Faculty of Science | Study plan (Version): Analytical Chemistry (2021) | Category: Chemistry courses | - | Recommended year of study:-, Recommended semester: Winter |
| Faculty: Faculty of Science | Study plan (Version): Inorganic and Bioinorganic Chemistry - specialization in Inorganic Materials (2021) | Category: Chemistry courses | - | Recommended year of study:-, Recommended semester: Winter |
| Faculty: Faculty of Science | Study plan (Version): Inorganic and Bioinorganic Chemistry - specialization in Bioinorganic Chemistry (2021) | Category: Chemistry courses | - | Recommended year of study:-, Recommended semester: Winter |
| Faculty: Faculty of Science | Study plan (Version): Organic Chemistry (2021) | Category: Chemistry courses | 1 | Recommended year of study:1, Recommended semester: Winter |
| Faculty: Faculty of Science | Study plan (Version): Bioinformatics (2021) | Category: Informatics courses | 3 | Recommended year of study:3, Recommended semester: Winter |
| Faculty: Faculty of Science | Study plan (Version): Chemistry - Analytical Specialist (2021) | Category: Chemistry courses | 2 | Recommended year of study:2, Recommended semester: Winter |