Course for international guest/part time students

Faculty

Faculty of Science

Organization

TTK Department of Inorganic Chemistry

Code

theoorgk20em

Title

Theoretical Organic Chemistry

Usual semester

Autumn

Published semester

2026/27/1

ECTS

4

Language

en

Learning outcomes

a) Knowledge - Concepts of mechanistic organic chemistry with the special regards to the electronic- and stereostructure and basic organic reactions.  Chemical bonding and its description by valence bond method and simplified MO theory at qualitative level are of pronounced importance. The basics of stereochemistry. Structure-reactivity relationships that can be interpreted by resonance structures and steric interactions. b) Abilities - The students possess the ability to recognise the mechanisms that can be explained in a unanimous way by the correct use of the general rules mainly of FMO- and HSBA theories discussed in detail in the lectures. Utilization of the acquired knowledge in the prediction of the regioselectivity and stereochemical outcome of certain organic reactions. Ability to find and to explore the information from the literature and the available chemical data bases. c) Attitude - The students are expected to seek to work on their own. They have to be ready to extend their knowledge in the discipline that can be exploited in the realisation of their professional purposes in their carreer. It is also desirable that the students show interest towards organic reaction mechanisms d) Autonomy and responsibility - Hold responsibility for making decisions on his/her study. Make a point of solving separately the study cases assigned by the lecturer to him/her. Responsible application of the knowledge acquired in the course of his/her study.

Course content

Frontier Molecular Orbital Theory and HSAB Theory HOMO–LUMO interactions and reactivity Orbital control of regio- and stereoselectivity Hard and soft acids and bases Applications to organic and organometallic reactions Aromaticity Hückel theory and the 4n+2 rule Aromatic, antiaromatic, and non-aromatic systems Structural, energetic, and magnetic criteria Aromaticity in heterocycles and reaction intermediates Linear Free-Energy Relationships and the Hammett Equation Transition-Metal Complexes and the Limitations of FMO and HSAB Theories Electronic structure and bonding in transition-metal complexes Applications of FMO and HSAB concepts Limitations of qualitative models and computational alternatives Pericyclic Reactions: reactivity, stereochemistry, mechanistic rationalization, synthetic applications, and illustrative examples Cycloadditions and cheletropic reactions Electrocyclizations and group-transfer reactions Sigmatropic rearrangements and valence bond isomerizations Radical Reactions Photochemical Processes Stereoelectronic Effects

Assessment method

Collokvium, K(5). The exam consists of two parts held during the same session in the exam period: first a written test, followed by oral questions.

Bibliography

Fleming, I. (2010). Molecular Orbitals and Organic Chemical Reactions (Reference Edition). Wiley Anslyn, E. V. & Dougherty, D. A. (2005). Modern Physical Organic Chemistry. MIT Press. Clayden, J.; Greeves, N.; Warren, S. (2012). Organic Chemistry (2nd ed.). Oxford University Press. Kirby, A. J. (2002). Stereoelectronic Effects. Oxford University Press (Oxford Chemistry Primers). Alabugin, I. V. (2016). Stereoelectronic Effects: A Bridge Between Structure and Reactivity. Wiley. Miessler, G. L.; Fischer, P.; Tarr, D. (2013). Inorganic Chemistry. (5th ed.) Pearson. Spessrad, G. O.; Miessler, G. L. (2015). Organometllaic Chemistry. (3rd ed.) Oxford University Press.

Programmes of the course