Organic Chemistry I.

Part I. Basic of organic chemistry, structure and chemistry of hydrocarbons

6.1. Basics of organic chemistry, structures of carbon compounds

Development of organic chemistry. Structure of molecules: theory of covalent bonding, rationalization of chemical bonds.                                                                                   3 h

Classification of organic compounds. Nomencalture of basic hydrocarbons. Nomenclature of aliphatic and aromatic hydrocarbons.  2 h

6.2. Configuration,  stereochemistry, conformation

Constitutional isomerisms. Stereoisomerism: E/Z isomerism, chirality, enantiomers and diastereomers. Inversion, retention and recemization. Conformation of aliphatic and alicyclic hydrocarbons.                                                                                                                     3 h

Substitutional and groupfunctional nomenclature. The main functional groups.                 2 h

6.3. Theory of reactions, theories of acid-base, HSAB and FMO theories

Types of organic reactions: substitutions, additions, eliminations and rearrangements. Nature of the reactions: multistep and concerted, ionic and radical reactions. The energy profile of reactions: transition state, parameters for activation, intermediates, concept of  kinetic and thermodynamic control. Acid-base equilibria. The concept of electrophilicity and nucleophilicity.                                                                                                                         3 h

Exercise for nomenclature of organic compounds.   2 h

6.4. Theory of redox and radical reactions, chemistry of paraffins

Rationalizing the oxidation number. Preparation of paraffins and cycloparaffins by reduction, methods for forming carbon-carbon single bonds. Physical properties, radical reactions and oxidation of paraffins and cycloparaffins.                                                                                   3 h

Exercise for the CIP-system.     2 h

6.5. Reactivity of olefines and acetylenes, electrophilic addition, oxidation and polymerization

 Electrophilic addition and radical reactions of olefines. Reactions of 1,3-dienes. Electrophilic addition and radical reaction of acetylene derivatives. Substitution and adddition reactions of conjugate bases of acetylene derivatives.                                                                                   3 h

Preparation of paraffins and cycloparaffins. Exercise for oxidation number. Reactions of paraffins. Conformation of paraffins and cycloparaffins.                                                  2 h

6.6. Reactivity of monocyclic aromatic compounds, electrophilic substitution

The structure of benzene, aromaticity and aromatic character. The mechanism of electrophilic substitution, halogenation, nitration and sulphonation, Friedel-Crafts alkylation and acylation. Orientation rules.                                                                                                                 3 h

Preparation and reactions of olefines. E/Z nomenclature of olefins. Elimination reactions. Preaparation and reactions of acetylenes.                                                                         2 h

Part II. Compound containing carbon-heteroatom single bonds

8.7. The theory of substitution and elimination

The mechanisms of aliphatic nucleophilic substitutions and eliminations, their regio- and stereochemistry. Factors influencing these reactions. Ambident nucleophiles. Aromatic nucleophilic substitution.                                                                                                            3 h

Test 1.: Nomenclature. Preparation, reactions, conformation and configuration of aliphatic and cyclic paraffins. Preparation and reactions of olefines. Regio- and stereoselectivity. Preparation and reactions of acetylenes.                                                                             2 h

8.8. The chemistry of halogen compounds, alcohols, phenols and ethers

The physical properties of halogen compounds, alcohols, phenols and ethers. Acidity and basicity of these compounds. Reactions of halogen compounds with metals. Preparation and reactions of alcohols, phenols and ethers.                                                                                  3 h

Preparation and reactions of aromatic compounds. Exercises for SEAr and SNAr reactions.    2 h

8.9. The chemistry of nitro compounds and amines

Preparation and reduction of nitro compounds. The structure, physical and basical properties of amines. Preparation and reactions of amines.                                                                   3 h

Preparation and reactions of halogen compounds, alcohols, phenols and ethers. Exercises for substitution and elimination reactions.   2 h

Part III. Compound containing carbon-heteroatom multiple bonds

8.10. Reduction and oxidation of alcohols, carbonyl compounds and carboxylic acid derivatives

Preparation of carbonyl compounds and carboxylic acids by oxidation. Preparation of alcohols and carbonyl compounds by reduction. Using Grignard and related reactions for the preparation of alcohols and carbonyl compounds. Using Friedel-Crafts and related reactions for the preparation of aromatic carbonyl compounds.                                                              3 h

Preparation and reactions of nitro compounds. Exercises regarding pKa.             2 h

8.11. Reactivity of carbonyl compounds, carboxylic acids and carboxylic acid derivatives

Comparison of the reactivities of aliphatic and aromatic carbonyl compounds, carboxylic acids and carboxylic acid derivatives - nucleophilic addition and nucleophilic addition-elimination reactions. Preparation and reactions of α,β-unsaturated carbonyl compounds and carboxylic acids. Inverse reactions.                                                                                   3 h

Test 2.: Preparation and reactions of aromatic compounds.  Orientation rules. Preparation and reactions of halogen compounds. Mechanism, regio- and stereoselectivity of substitution and elimination reactions. Preparation and reactions of alcohols, phenols, ethers, nitro compounds and amines.                                                                                                                    2 h

6.12. Oxo-enol tautomerism, carboxylic acids

Oxo-enol tautomerism. Comparison of the reactivities of oxo-enol tautomers. Reactions taking place with the conjugate bases of carbonyl compounds and carboxylic acid derivatives (at α-position). The chemistry of dicarbonyl and related compounds.                                        3 h

Supplementary test 1. or                                                                                                                                   2 h

6.13. Chemistry of carboxylic acids and carboxylic acid derivatives

Physical and chemical properties of carboxylic acids. Preparation and reactions of dicarboxylic acids - decarboxylation reactions. Carboxylic acid derivatives: preparation and reactions of ketene, acyl halides, acid anhydrides, azides, esters, amides, nitriles, imid acid esters - nucleophilic addition and nucleophilic addition-elimination reactions.                                   3 h

Preparation and reactions of carbonyl compounds. Preparation of carboxylic acids. Reactions of carbonyl compound and carboxylic acids.                                                                                    2 h

Extra supplementary test 1. or 2.                                                                                                                   2 h

7. Method of education: