Learning objectives
<br />The aim of the course is to provide basic knowledge on the interpretation and evaluation of the structure, physical properties and reactivity of organic molecules. Moreover, the students will learn the basic tools for the comprehension of the kinetic and thermodynamic aspects of the organic reactions as well as the stereochemistry of the molecules involved in such reactions. All these aspects will be discussed in the context of the chemistry of polymers, carbohydrates, aminoacids, proteins, and lipids. A short overview of the chemistry of metabolism will be also discussed.
Course unit content
<br />Conjugate dienes: nomenclature and reactivity. Electrophilic addition to conjugate dienes: experimental evidences, mechanism, thermodynamic and kinetic control (addition 1,4 and 1,2). Cycloaddition reactions of Dies Alder: synthesis of six-termini rings. Definition of diene and dienophile in the Dies Alder reactions. Effect of the electron withdrawing and electron donating groups on the reaction kinetic. Synthesis and nomenclature of bicyclic products obtained through Dies Alder reactions. Regioselectivity and stereoselectivity of the Dies Alder reactions. Mechanism of the pericyclic reactions. Dies Alder reactions catalysed by Lewis acids. Introduction to the chemistry of organic polymers. Classification and nomenclature of organic polymers. Physical-Chemical properties of organic polymers. Thermoplastic and thermosetting polymers. Mechanism of the step growth (SG) polymerization. Mechanism of the chain growth (CG) polymerization: initiation, propagation, and termination. Polymerization with cationic and anionic mechanism. Carbohydrates: definition and physical properties. Monosaccharides: nomenclature, stereoisomerism (D and L isomers), and Fisher projections. Classification of D-monosaccharides as aldose and ketose. Formation of hemiacetals: open and closed form of D-glucose and D-fructose. Pyranosic and furanosic ring forms: Haworth and chair projections of monosaccharides. Anomers and mutarotation of monosaccharides. Reactions of monosaccharides: formation of glycosides and N-glycosides. Mechanism of glycoside formation (acetals). Exhaustive methylation and oxidation reactions of monosaccharides. Reaction with bromine in basic condition. Tollens', Fehling's and Benedict's tests for reducing sugars. Reaction with periodic acid: determination of the ring structure of monosaccharides. Disaccharides: classification and nomenclature. Structure of maltose, lactose and sucrose. Polysaccharides: classification and nomenclature. Structure of starch (Amylose and amylopectin), glycogen and cellulose. Alpha-1,4-, alpha-1,6-, and beta-1,4-glycosidic bonds. Classification of lipids. Triglycerides: structure, fatty acids composition, and physical properties. Soaps and detergents derived from triglycerides. Prostaglandins: classification, structure, and activity. Sterols: classification, structure, and activity. Biosynthesis of cholesterol. Phospholipids and liposoluble vitamins. Aminoacids: structure, stereoisomerism, and nomenclature. Aminoacids derived from protein. Natural occurring L-aminoacids. Acid base properties of aminoacids. Titration of aminoacids. Isoelectric point (PI) and Zwitterionic form of aminoacids. Polypeptides and proteins. Primary structure of proteins: aminoacids analysis, restriction enzymes, cyanogen bromide. Determination of the protein sequence through Edman's degradation. Secondary structure of proteins: beta-sheets and alpha-helix. Structure tertiary and quaternary of proteins. The molecules of metabolism: ATP/ADP/AMP, NAD+/NADH, and FAD/FADH2. Fatty acids: a source of energy for the organisms. Beta-oxidation of fatty acids: activation and mechanism. Nucleic acids: a short introduction.
Bibliography
<br />Brown & Foote - Chimica Organica - 2nd edition - Edises<br />Brown & Poon - Introduzione alla Chimica Organica - 3rd Edition - Edises
Teaching methods
<br />The final evaluation of the student skills will be carried out through an oral examination.
