Organic Chemistry

1.) Structure of organic molecules. VSEPR and VB theories. Rationalization of chemical bonding using hybridization, conjugation, hyperconjugation, inductive and mesomeric effects. Molecular orbitals. Hückel MO theory. Symmetry of molecular obbitals. Frontier molecular orbitals. Rationalization of chemical bonding by molecular orbitals.

2.) Pericyclic reactions. Cycloaddition and cycloreversion. Diels-Alder reaction. Dipolar cycloaddition. Woodward-Hoffmann rule. Sigmatropic rearrangements. Electrocyclic (ring closing and ring opening) reactions. Sigmatropic hydrogen shifts. Thermal and photochemical reactions. Reactions accompanied by rearrangements.

3.) a.) Configuration and conformation. Chirality, symmetry elements. Static and dynamic stereochemistry. Prochirality.

b.) Thermodynamics and kinetics of organic reactions. Kinetic isotope effects.

c.) Properties of acids and bases, pK_a and pK_b values. Hard and soft nuclephiles and electrofiles. Ambident nucleophiles. Orbital controlled and charge controlled reactions.

Kornblum’s rule.

4.) a.) Factors influencing aliphatic and aromatic nucleophilic substitutions. Stereochemical questions.

b.) Elimination (α and β, respectively) reactions. Preparation of carbenes, ylides and olefines. Regio- and stereoselectivity.

5.) a.) Electrophilic addition to olefines, diolefines and acetylenes. Regio- and stereoselectivity.

b.) Electrophilic aromatic substitution. Effects of the substituent and substituens, respectively in the aromatic ring for the rate of the reactions. Rationalization of the orientation effect of the substituents.

6.) a.) Nucleophilic addition and nucleophilic addition-elimination to carbonyl group and conjugated oxo-compounds, respectively. Factors influencing reactivity.

b.) Tautomerism of oxo-compounds and their analogues. Reactions proceeding  through enols and enolates, respectively as intermediates.

7.) Reactivity of carboxylic acids, carboxylic and carbonic acid derivatives. Acylation mechanisms. Comparison of acylation abilities of carboxylic acid derivatives

8.) Preparation and synthetic applications of organic radicals. Reactions proceeding  through radicals and radical anions, respectively as intermediates. Radical, anionic and cationic polymerizations. Polycondensation reactions.

9.) Applications of protecting groups in chemical synthesis.

10.) Using of easily available natural enantiopure compounds (chiral pool) (amino acids, sugars, hydroxy acids, alkaloids etc.) for the  preparation of optically active materals. Bio- and chemocatalysis, regio- and stereoselectivity. Applying enantioselective methods for the preparation of compounds containing more than one chiral centers.

11.) Synthetic applications of organic boron-, sulfur- and phosphorus compounds. Organometallic compounds in organic synthesis. Preparation and applications of organometallic compounds of alkali (Na, Li) and alkaline earth (Mg) metals. Organometallic compounds of zinc and copper. Reactions catalyzed by palladium (II) and palladium (0).

12.) Using heterocyclic compounds in organic synthesis.

13.) Special techniques in organic synthesis. Microwave-assisted synthesis. Solid-supported chemical synthesis. Basics of combinatorial chemistry.

Theory and applications of molecular recognition including enantiomeric recognition in analytical chemistry and separation techniques.