Organic chemistry 0600-S1-CM-CO

Lecture
The lecture provides a comprehensive introduction to organic chemistry, beginning with its essence and the significance of carbon compounds in human life and industry. It will present the main classes of hydrocarbons, their structures, properties, and methods of synthesis. Particular emphasis will be placed on reaction mechanisms and structural analysis of organic compounds.
1. Alkanes and Cycloalkanes
Alkanes: Discussion of alkanes as the fundamental class of hydrocarbons—their laboratory and industrial synthesis (including the Bergius and Fischer–Tropsch processes), natural sources such as crude oil and natural gas, and their processing (refining), with special attention to the influence of octane and cetane numbers on fuel quality. Detailed coverage of alkane conformation, combustion, and the mechanism of free-radical chlorination and bromination.
Cycloalkanes: Exploration of ring structure and stability (Baeyer strain theory), cyclohexane conformations, and the stereochemistry of its substituted derivatives.
2. Alkenes and Alkynes
Alkenes: Presentation of alkene structure and nomenclature, along with their laboratory synthesis methods (alcohol dehydration, E2 elimination, and debromination). Special attention will be given to electrophilic addition mechanisms, Markovnikov’s rule, exceptions to that rule, and reactions such as epoxidation, hydration, bromination, and oxymercuration–demercuration. Oxidative degradation of alkenes (ozonolysis and oxidation with KMnO₄) will also be covered.
Alkynes: Discussion of physicochemical properties, the acidity of terminal alkynes, their addition reactions, and synthesis mechanisms (including eliminations and tautomeric shifts).
3. Arenes
Structure of benzene, the criteria of aromaticity (Hückel’s rule), and the differences in the chemical reactivity of benzene compared to other hydrocarbons. Coverage of electrophilic aromatic substitution reactions (bromination, chlorination, nitration, sulfonation, and Friedel–Crafts alkylation/acylation) and the directing effects of substituents. Particular attention to benzene derivatives and side-chain reaction mechanisms. In addition, polycyclic aromatic compounds, annulenes, and aromatic heterocycles will be introduced.
4. Organometallic Compounds
Discussion of lithium, magnesium, boron, zinc, mercury, and copper organometallics—their preparation, structure, properties, and wide applications in organic synthesis.
5. Alcohols, Phenols, and Ethers
Presentation of the structure, nomenclature, preparation methods, and characteristic reactions of alcohols, phenols, and ethers (including crown ethers).
6. Reactions and Mechanisms
Overview of fundamental organic reaction mechanisms, including SN1, SN2, E1, and E2, along with their kinetics, stereochemistry, and energy profiles. Detailed discussion of the competition between nucleophilic substitution and elimination, as well as the influence of factors such as substrate structure, nucleophile type, and leaving group quality.
7. Stereochemistry and Isomerism
Examination of different types of isomerism, with particular attention to optical isomerism and stereoisomerism. Concepts such as enantiomers, diastereomers, meso forms, and racemates will be explained, including their resolution. The lecture will clarify how a polarimeter works, the concept of specific rotation, and how the spatial structure of compounds affects their properties (e.g., aroma).
Laboratory
In the laboratory sessions, students acquire practical skills in fundamental laboratory techniques essential for the isolation, purification, and synthesis of organic compounds. The classes focus on the practical execution of key organic chemistry reactions, including nucleophilic substitutions (SN1 and SN2), elimination reactions, and the Williamson ether synthesis. Students also learn to analyze and interpret their results and to follow laboratory safety protocols.
Exercises
These sessions aim to reinforce the lecture material through problem-solving and the analysis of specific examples. Topics include the methods of writing organic structures, principles of nomenclature, types of hybridization, and classification of chemical bonds. Special emphasis is placed on issues related to various types of isomerism, typical reactions, and the reaction mechanisms discussed in the lectures.