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Lecturer(s)
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Vícha Robert, doc. Mgr. Ph.D.
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Rouchal Michal, doc. Ing. Ph.D.
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Course content
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1. Paremeters of molecular geometry. Chemical bond. Model of covalent bond. Bond strength and length, valence angles, torsion and dihedral angles - scope and limitations. 2. Molecules in space. Electron structural formula and geometry derivation - VSEPR. 3. Symmetry. Symmetry elements. Point groups of symmetry. Space groups of symmetry. Relationships between macroscopic and molecular symmetry - philosophical aspects. 4. Chemical models. 5. Chirality. Pasteur versus Vant Hoff, optical purity and racemic modifications. Further types of chiral objects: axial and planar chirality, helicity. 6. Interpretation of spectra concerning symmetry (with force on NMR). 7. Conformation - conformation analysis and equilibria. 8. Conjugation, aromaticity, non-aromaticity, anti-aromaticity. 9. Frontier orbitals theory, LUMO, HOMO, symmetry of FO. 10. Pericyclic reactions. Woodward-Hoffmann rules, Fukui theory of frontier orbitals interaction, Dewar-Zimmerman theory of aromatic transit states. 11. Electrocyclic reactions. 12. Cycloaddition reactions. 13. Dipolar cycloadditions. 14. Sigmatropic rearrangements, ene-reactions.
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Learning activities and teaching methods
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Lecturing, Practice exercises, Students working in pairs
- Home preparation for classes
- 14 hours per semester
- Participation in classes
- 42 hours per semester
- Preparation for course credit
- 34 hours per semester
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| learning outcomes |
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| Knowledge |
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| The student has knowledge about symmetry as important property not only of molecules but also macroscopic objects. |
| The student has knowledge about symmetry as important property not only of molecules but also macroscopic objects. |
| The student also deepens knowledge about pericyclic reactions - a phenomenal part of organic chemistry. |
| The student also deepens knowledge about pericyclic reactions - a phenomenal part of organic chemistry. |
| Skills |
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| The student can find the main symmetry elements of the given molecule. |
| The student can find the main symmetry elements of the given molecule. |
| With the help of a key, the student can determine the symmetry point group of any 3D object, including molecules. |
| With the help of a key, the student can determine the symmetry point group of any 3D object, including molecules. |
| The student can estimate the number of signals in NMR spectra based on the symmetry of molecules. |
| The student can estimate the number of signals in NMR spectra based on the symmetry of molecules. |
| The student can describe the progress of the main groups of pericyclic reactions (cycloaddition reactions, electrocyclization reactions, sigmatropic rearrangements) both in terms of product constitution, regioselectivity and stereoselectivity. |
| The student can describe the progress of the main groups of pericyclic reactions (cycloaddition reactions, electrocyclization reactions, sigmatropic rearrangements) both in terms of product constitution, regioselectivity and stereoselectivity. |
| teaching methods |
|---|
| Knowledge |
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| Lecturing |
| Lecturing |
| Dialogic (Discussion, conversation, brainstorming) |
| Dialogic (Discussion, conversation, brainstorming) |
| Skills |
|---|
| Students working in pairs |
| Students working in pairs |
| Practice exercises |
| Practice exercises |
| assessment methods |
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| Knowledge |
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| Grade (Using a grade system) |
| Grade (Using a grade system) |
| Written examination |
| Written examination |
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Recommended literature
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Červinka, O. Chiralita a pojmy s ní související. Chem. Listy 93, 294-305, 1999.
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Fišer, Jiří. Úvod do molekulové symetrie : (Aplikace teorie grup v chemii). 1. vyd. Praha : SNTL, 1980.
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Fleming, I. Hraniční orbitaly a reakce v organické chemii. Praha : SNTL, 1966.
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Fleming, I. Pericyclic Reactions. Oxford: Oxford University Press, 2004. ISBN 0-19-850307-5.
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KETTLE, S.F.A. Symmetry and Structure: Readable Group Theory for Chemists. 3rd Ed.. Wiley, 2007. ISBN 978- 0470060407.
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LEE, J.K., TANTILLO, D.L. Reaction Mechanism Part (ii) Pericyclic Reactions. Annu. Rep. Prog. Chem., Sect. B, 104, 260-283, 2008.
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McMurry, John. Organická chemie. Vyd. 1. Brno : VUTIUM ; Praha : Vysoká škola chemicko-technologická v Praze, 2007. ISBN 978-80-214-3291-8.
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TANTILLO, D.J., LEE, J.K. Reaction Mechanism Part (ii) Pericyclic Reactions. Annu. Rep. Prog. Chem., Sect. B, 103, 272-293, 2007.
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