B016510 - ORGANIC CHEMISTRY I

Italian

The carbon and its hybrid orbitals. Nature of sigma and pi bonds. Aliphatic hydrocarbons: structure, properties nomenclature, isomerism and conformational analysis. Aromatic hydrocarbons: the concept of resonance. Acids and bases in organic chemistry. Organic compounds containing hetero atoms. Stereoisomerism: chirality, enantiomers and diastereoisomers. Reaction mechanisms: additions, eliminations and substitutions. Carbonyl and carboxylic derivatives: properties and reactivity.

SMITH, J.G.: "CHIMICA ORGANICA" McGraw-Hill (MI);
ALLINGER N. L., CAVA M. P., et al. : "CHIMICA ORGANICA" Zanichelli (BO).
McMURRY J.: "CHIMICA ORGANICA" Piccin (PD);
SOLOMONS G.: "CHIMICA ORGANICA" Zanichelli (BO);
BROWN, FOOTE: "CHIMICA ORGANICA" EdiSES (NA);
STREITWIESER A., HEATHCOCK C. H., KOSOWER E. M.: "CHIMICA ORGANICA" EdiSES (NA).

Among course's goals there are the knowledge of stucture and properties of simple organic molecules and the ability of manenging basic principles of organic molecules tranformations in substitution, elimination and addition processes.

General chemistry is mandatory

Blackboard and transparencies are commonly used together with molecular models.

Friday morning or any other day on appointments

Oral exam

Structure and properties of organic molecules (3 credits): The carbon atom and its hybrid orbitals (sp3, sp2, sp) in organic compounds. Structural consequences of hybridization. Sigma and pi bonds. Isomers and conformers. Relationship between structure and properties of organic compounds. Inter and intra-molecular interactions: Van der Waals, dipole-dipole, and Hydrogen bonding. The role of resonance and delocalization in organic chemistry. Acids and bases. Fundamental organic functional groups.
Organic stereochemistry (1 credit): chirality and symmetry. Organic molecules ad rigid objects. Role and impact of right-handed and left-handed molecules. Stereoisomers, diastereoisomers and enantiomers. Racemic mixtures.
Organic reactivity part 1 (3 credits): Organic reactions kinetic and mechanism. SN2 and SN1 nucleophilic substitutions, E2 and E1 elimination: mechanism, products and stereochemical features. Addition to carbon-carbon and carbon-heteroatoms multiple bonds. Electrophilic aromatic substitution (SEAr): mechanism and reactivity of benzene and substituted arenes. Reactivity of carbonyl and carboxylic compounds: addition, addition-elimination, alpha-substitution.
Chemistry of biomolecules (1 credit): Amino acids, sugars and lipids: structure, properties and reactivity. Peptides, proteins, disaccharides and polysaccharides: structure, properties. An overview on the role of these biomolecules in biological processes.
Organic reactivity part 2 (2 credits): Functionalizations of arenes different from SEAr. Reactivity of conjugated systems: 1,2 vs 1,4 additions. Oxidations and reductions. Wittig reaction. Diels-Alder reaction. Radical reactions. The polymers