1) Organic molecules in space. Constitution - configuration - conformation. Stereochemistry - stereogenic centre, chirality, optical activity. Nomenclature of stereoisomers (R/S, E/Z, cis/trans). 2) Ractive species in organic chemistry - radicals (formation, stability, mechanism of radical substitution on alkanes, radical additions on C=C bond); carbocations (rate of formation, stability ways of stabilization); carbanions. 3) Disulfide bridges; H-bonds; ion-ion, ion-dipole, dipole-dipole, pi-pi interactions; disperse forces; hydrophobic effect and role of these intermolecular interactions on structure stabilization of biopolymers. 4) Nucleophilic substitution on saturated C-atom - SN1, SN2, SNi, characterization of the mechanisms, related stereochemistry (inversion/retention of configuration, racemization). 5) Eliminations - Hofmann elimination (quaternary ammonium hydroxides); dehydration, dehydrogenations, dehydrohalogenations; syn and anti eliminations. 6) Aromaticity, non-aromaticity and antiaromaticity - structural and energetic aspects; heterocyclic aromatics (basicity of N-containing heterocycles - pyrrole vs pyridine); other non-benzoic aromatic molecules and ions (azulene, indole, cyclopropenylium, cycloheptatrienylium, cyclopentadienide); comparison of alkene and arene reactivity. 7) Electrophilic aromatic substitution - mechanism, regioselectivity driving effect of substituents, examples. 8) Electrophilic additions on unsaturated bonds (syn and anti mechanism). 9) Nucleophilic additions on C=O (addition of O-/N-/C-nucleophiles, aldolisation). 10) Nucleophilic substitution on unsaturated C-atom of aromatics (addition/elimination and elimination/addition mechanism) and carbonyl compounds (relationships between functional derivatives of carboxylic acids, Claisen and related reactions). 11) Acidity and basicity in organic chemistry (definition, strength and structural origin). 12) Redox reactions in organic chemistry - determination of oxidation state of atoms in organic compounds; chemical transformations: alkanes-alkenes-alkynes; alcohols-aldehydes-carboxylic acids; sulfides-sulfoxides-sulfones; benzene diols-benzoquinones; nitro-nitroso-hydroxylamine-diazo-hydrazines. 13) Amino acids (proteinogenic amino acids, other aminoacids, acidobasic properties, isoelectric point). 14) Proteins (peptide bond parameters, four levels of protein structure characterization). 15) Saccharides - structural types, stereochemistry (epimers, anomers, mutarotation); reduction and oxidation (C1 and C-omega oxidation); alkylation, substitution of OH groups (NH2); N- and O- glycosides. 16) Di-, oligo- and polysaccharides - reducing and non-reducing disaccharides; structure and properties of polysaccharides (amylose, amylopectin, glycogen, inulin, cellulose, chitin, chitosan, hyaluronic acid) 17) Catabolism of glucose (glycolysis and Krebs' cycle). 18) Biologically relevant esters (acylglycerols, phospholipides, nucleoside-phosphates, acetylcholin). 19) Purine and pyrimidine derivatives (basis of nucleic acids, nucleosides, nucleotide, structure and role of ATP and Ac-CoA). 20) Biologically relevant redox systems, structure and functions (glutathione, lipoic acid, FAD/FMN, NAD+, NADP+, ubiquinones, ascorbic acid).
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