ORGANIC CHEMISTRY B
Learning outcomes of the course unit
The objective of the course is to give the tools for the comprehension of the chemical behaviour of polyfunctional organic molecules.
Knowledge of the arguments developed in the Organic Chemistry A course
Course contents summary
Benzene structure and aromaticity concept: phenols and anilines, electrophilic aromatic substitution. Enolates: aldol condensation, intramolecular aldol condensation, mixed aldol condensation, kinetic and thermodynamic control; Claisen condensation, mixed Claisen condensation. Enamines: alkyation and acylation. The acetoacetic and malonic syntheses. Addition to alfa,beta-unsaturated carbonyl compounds: the Michael reaction. Conjugates dienes: 1,2 and 1,4 addition reactions, kineticand thermodynamic control. The Diels-Alder reaction: mechanism and stereochemistry. Polymers: nomenclature, classification and properties (melting point, crystallinity, amorphism). Condensation polymers: polyamides, polyesters, polycarbonates, polyurethanes, epoxy resins. Addition polymers: chain growth mechanism (initiation, propagation, termination) and transposition phenomena; the Ziegler-Natta catalysts. Carbohydrates: classification, the Fisher and Howart formulas for monosaccharides representation; glycosides formation. Disaccharides, oligosaccharides and polysaccharides. Lipids: classification. Triglycerides, prostaglandins, phospholipids and soluble vitamins. Steroids and biliary acids; the cholesterol biosynthesis. The organic chemistry of the metabolism: the fourreactions of the beta-oxidation of fat acids and the ten reactions of the glycolysis. Amino acids: nomenclature and classification; acid-base properties; amino acids distribution equilibriums as function of pH; isoelectric point of amino acids and gel electrophoresis. Polypeptides and proteins: primary, secondary, tertiary and quaternary structures; primary structure polypeptide determination: chemical digestion and chromatographic analysis, use of restriction enzymes and of cyanogen bromide, Edman degradation; polypeptide synthesis. Nucleic acids: nucleosides and nucleotides; DNA structure; the ribonucleic acids.
Brown & Foote, "Chimica Organica" Seconda Edizione, EdiSES