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).
Learning Objectives
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.
Prerequisites
General chemistry is mandatory
Teaching Methods
The core of the lesson is given at the blackboard with chalk. A contemporary video projection is used for complex schemes and numeric table, this material is published for all the students on the Moodle platform. Molecular models are commonly used to demonstrate the organic molecules structure and transformations.
Further information
Tutoring: Friday morning or any other day on appointments.
Email: stefano.menichetti@unifi.it
Type of Assessment
Every year there are 5 exam sections plus 2 during the possible periods of ‘didactical silence’ in November and April. The final exam is an oral discussion dedicated to pointed out knowledge and ability of the students in describing the structure, properties and reactivity of the organic compounds with a particular emphasis toward the stereochemical implications of chemical transformations.
Course program
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