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BIOORGANIC CHEMISTRY PROGRAM 1. Organic chemistry – chemistry of the carbon atom. Valence of carbon, Chemical bond, hybridization, sp3, sp2, sp hybridization, geometry of the molecules. Isomers. 2. Alkanes, IUPAC and common nomenclatures, chemical properties, methods of preparation, Wurtz reaction, radical substitution reactions. Stability of radicals. 3. Alkenes. IUPAC nomenclature, chemical properties, methods of preparation, electrophilic addition reactions, Markovnikov and Zaitseff rules, antiMarkovnikov addition of HBr. Polymerization. Z-, E- isomeres. 4. Alkynes. IUPAC nomenclature, chemical properties, methods of preparation, reactions of terminal alkynes, addition of acetic acid, ethanol, hydration reaction. PVA. 5. Dienes. Types of dienes. IUPAC nomenclature, methods of preparation. 1,2- and 1,4 addition of halogens, acids and water to conjugated dienes. Divinyl and isoprene polymerization, natural and artificial rubber. 6. Aromatic compounds. IUPAC nomenclature, methods of preparation. Aromaticity. Huckel rule. Heteroaromatic compounds –pyrrole and pyridine. Electrophilic substitution reactions. Nitration, halogenation, Friedel-Krafts alkylation and acetylation. 7. Effects of substituents on further substitution. Ortho- and para-, meta directing substituents. Effect of substituents on reactivity. Side-chain reactions of alkylarenes. Synthesis of 3- and 4- nitroaniline. 8. Alkyl and aryl halides. IUPAC nomenclature, methods of preparation. Nucleophilic substitution reactions (SN1, SN2). Dehydrohalogenation reaction. Reactivity of alkyl and aryl halides in SN reactions. Vinyl chloride. Grignard reagents. 9. Alcohols and phenols. Nomenclature, methods of preparation, chemical properties. Acidity of alkyl and aryl alcohols. Polyhydric alcohols. 10. Aldehydes and ketones. Structure of carbonyl group. Nomenclature. Chemical reactions on carbonyl carbon and -carbon atom. Aldol condensation, oxidation and reduction. 11. Amines. Structure of amines, nomenclature, methods of preparation. Basicity of amines. Reactions of amines. Reaction of primary, secondary and tertiary amines with nitrous acid. Reactions of aromatic amines on amino group and aromatic ring. 12. Carboxylic acids. Nomenclature, trivial names. Acidity. Methods of preparations. Chemical properties. Esterification reaction, Hell-Volhard-Zelinsky reaction. 13. Acid derivatives. Acid halides, anhydrides, amides, esters, urea. Praparation and chemical reactions. 14. Hydroxy and amino acids. Nomenclature. Methods of preparation. Action of heat . Reactions on functional groups. Synthesis of dipeptides . 15. Carbohydrates. Classification. Glucose, mannose, galactose, fructose. Mutarotation. Killiani-Fisher synthesis. Reactivity. Oxydation and reduction reactions. 16. Disaccharides. Reducing and non-reducing sugars. Sucrose, maltose, cellobiose, lactose. Starch, cellulose.