300324 VO Organic Chemistry for Molecular biology (2013W)

Recommended Book: Harold Hart -

"Organic Chemistry"

I: Saturated Hydrocarbons

IUPAC nomenclature, isomers, properties, conformation, halogenation of alkanes.

II. Unsaturated Hydrocarbons

Alkenes and cycloalkenes: Nomenclature, cis-trans isomers, structure, properties, synthesis, electrophilic addition of HBr, Br2, HOX, rule of Markownikow, hydroboration, nucleophilic addition to C=C bonds with an electron-withdrawing substituent, hydrogenation, oxygen transfer reactions.

Chirality: R/S and D/L nomenclature, absolute configuration, racemate, enantiomers, meso compounds, resolution.

Alkynes: Nomenclature, structure, properties, preparation and reactions.

III. Aromatic compounds

Resonance, resonance structures, aromaticity, nomenclature, electrophilic substitution in benzenes, I- and M-effect, directing effect of substituents.

IV. Halogenated alkanes

Nomenclature, properties, polyhalogenated compounds, preparation, SN1- and SN2-reaktions; E1- and E2-eliminations, organometallic compounds (Mg, Li); methylation in biosphere.

V. Alcohols, phenols, and ethers

Nomenclature, properties, synthesis and reactions of alcohols, oxidation of alcohols in the cell, phenols as antioxidants, quinone/hydroquinone; ethers.

VI. Aldehydes and ketones

Nomenclature, properties, synthesis, nucleophilic additions to the carbonyl group, addition of hydrogen cyanide, water, alcohols, formation of acetals, addition of hydrogen, organometallic compounds, nitrogen nucleophiles, oxidation of aldehydes, enolisation of aldehydes and ketones, aldol reaction and condensation.

VII. Carboxylic acids and derivatives

Nomenclature, properties, synthesis, acidity, nucleophilic substitutions at the carbonyl group of carboxylic acids and their derivatives, esters and thioesters, amides, reductions, addition of organometallic compounds to esters, Claisen condensation, reactions of thioesters in biochemistry.

VIII. Amines and related compounds

Nomenclature, structure, properties, synthesis, acylation, alkylation, reactions of amines with nitrous acid, dehydrogenation of amines in cell.

IX. Derivatives of carbonic and phosphoric acid

Phosgen, chloroformates, carbonates, urea.

Formation and reactions of ATP, activation of carboxylic acids.

X. Synthesis of polymers

General remarks, polymerisation, radical polymerisation, polycondensation, and polyaddition.

XI. Aminoacids, peptides, and proteins

Proteinogenic aminoacids, reactivity of SH group of cysteine, peptides, ninhydrin reaction, synthesis of peptides, protecting groups for amino and carboxyl group, formation of peptide bonds, proteins, determination of C- and N-terminal aminoacids, Sanger reagent, sequencing of proteins, Edmann degradation, structure and biosynthesis of proteins.

XII. Carbohydrates, nucleosides and nuleotides

Monosaccharides, nomeclature and stereochemistry, cyclic acetals, anomers, reactions of monosaccharides, disaccharides (maltose, cellobiose, lactose, saccharose), polysaccharides (starch, cellulose), nucleosides, and nucleotides.