Organic Chemistry for Bioengineers

Molecular structure: Theory of the covalent bonding. Orbitals, hybridization, non-localized bonds.

Stereochemistry, conformation: Structural, geometric and stereo isomerism. Enantiomers and diastereomers. The CIP rule. Inversion, retention and racemization. Conformation of open-chain and cyclic hydrocarbons.

Reactions, acid-base-, HSAB- and FMO theories: Single step and multistep reactions. Energy profile of reactions, kinetic and thermodynamic control. Acid-base equilibriums, Brønsted-, Lewis-, HSAB- and FMO-theories. The electrophilicity and nucleophilicity.

Saturated hydrocarbons, redox and radical reactions: Redox reactions, the SET mechanism. Physical and chemical behavior of saturated hydrocarbons, the radical reactions.

Open-chain unsaturated hydrocarbons: Physical and chemical behavior of unsaturated hydrocarbons, olefins and acetylenes.

Aromatic hydrocarbons: Aromaticity, structure of mono- and polycyclic aromatic hydrocarbons. Biphenyl and triphenylmethane, the atrop isomerism. Aromatic electrophilic and nucleophilic substitutions.

The theory of substitution and elimination: Mechanism, region- and stereochemistry of substitution and elimination, the ambident nucleophiles.

Chemistry of compounds with carbon heteroatom single bond: Physical and chemical behavior of halogen compounds, alcohols, phenols, ethers and amines.

Redox reactions of oxygen containing compounds: Oxidations of alcohols and oxo compounds, reductions of derivatives of carboxylic acids and oxo compounds. The Grignard- and the Canizzaro reactions.

Reactivity of carbonyl compounds: The structure of the carbonyl group. Reactions of aldehydes, ketones, carboxylic acids and derivatives of carboxylic and carbonic acids.

Tautomerism of carbonyl compounds. Dioxo and related compounds: The oxo–enol and ring–chain tautomerism of carbonyl compounds. Reactions of the enolates. Reactions of diethyl malonate and ethyl acetoacetate.

Acids and bases: Acidity and basicity of amines, alcohols, phenols, carboxylic acids and amino acids.

Stereochemistry: The Emil Fischer convention. Asymmetric synthesis. Resolution.

Heterocycles: Five- and six-membered heterocycles. Pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyridine, pyrimidine, purine.