Organic Chemistry II.

Part I. Chemistry of special families of compounds

6.1. Reactivity of carbonyl group

Reactivity of compounds containing a carbonyl group.                                                          3 h

6.2. Derivatives of carbonic acid

Derivatives of carbonic acid: chlorides, esters, urethanes. Urea and its derivatives. Carbon disulfide, xanthogenates, thiourea and its derivatives. Isocyanic acid, isothiocyanic acid and their derivatives. Cyanamide, carbodiimide, guanidine and their derivatives.                                                                                                      3 h

6.3.Diazomethane, azo-, diazo-, diazonium and related compounds

Preparation and reactions of diazomethane and aromatic diazonium salts.            

Sulfur- and phosphor-containing compounds

Thiols, sulfides, sulfonium salts, sulfoxides, sulfones, sulfonic acids. Phosphines,

phophonium salts and phosphine oxides. The Wittig reaction.                                            3 h

6.4. Halogen, hydroxy and oxo acids and their derivatives

Preparation and reactions of α-, β-, γ-, and δ- substituted halogen, hydroxy, and oxo acids and their derivatives.                                                                                                                       3 h

6.5. Malonic acid ester and acetoacetic ester syntheses

Preaparation and using of acetylacetone, malonic acid ester and acetoacetic ester in organic synthesis.

Biological important hydroxy and oxo acids. Formation and degradation of saturated fatty acids in living organism.                                                                                                           3 h

 Part II. Lipids, amino acids, peptides, proteins, carbohydrates

6.6. Lipids

Main groups of biomolecules, their function in living organism. Types of lipids. Function of simple and complex lipids in living organism. Structure and function of terpenes and compounds containing steroid skeleton in living organism.

Stereochemistry

Effects of chirality, optical rotation, ORD. The Emil Fischer D/L convention. Compounds containing more than one chiral centers, meso compounds, pseudo asymmetry.                      3 h

6.7. Stereoselective reactions

Types and rationalization of asymmetric reactions. Resolution.                                           1.5 h

Test 1.                                                                                                                                   1.5 h

6.8. Monosaccharides

Aliphatic and lactol ring structure of monosaccharides, mutarotation. Aldose-ketose conversion. Reduction and oxidation of monosaccharides, sugar alcohols, sugar acids. Formation, degradation and reactions of monosaccharides. Srtucture and function of ascorbinic acid.                                                                                                         3 h

6.9. Oligosaccharides, polysaccharides

Structure, occurence and synthesis of oligosaccharides. Structure and occurence of polisaccharides.

Amino acids

Structure, physical and chemical properties, biochemical function of amino acids. Abbreviations according to convention. Synthesis of amino acids.                                  3 h

6.10. Peptides and proteins

Structure of peptide bond. Synthesis of peptides, protecting groups and coupling methods, solid-supported chemical synthesis. Classification and biochemical function of proteins. Primary, secondary, tertiary and quarternary structures of proteins. The Ramachandran diagram.                                                                                                                          3 h

 Part III. Polycyclic aromatic compounds, heterocyles nucleic acids.

6.11. Condensed and isolated polycyclic aromatic compounds, heterocycles

Structure, aromacity and reactions of naphthalene, anthracene, phenanthrene, fluorene. Chemichal properties, derivatives and reactions of diphenyl- and triphenylmethane.                                             1.5 h

Test 2.                                                                                                                                   1.5 h

6.12. Synthesis of heterocycles, five-membered heterocycles

Preparation of heterocycles. Structure, aromaticity and chemical reactions of furan, pyrrole and thiophene. Biochemical function of porphine skeleton. Structure, aromaticity and chemical reactions of azoles.                                                                                                    3 h

6.13. Six-membered heterocycles

Structure, aromaticity and chemical reactions of pyridine, diazines and their derivatives. Synthesis of papaverine.

Nucleotides

Preparation of bases of nucleic acids. Structure and chemical reactions of NAD+ (niacinamide) and FAD (vitamin B₂).                                                                             3 h