Organic Chemistry

The aim of the course is to supply the fundamental knowledge on the structure and reactivity of organic compounds. Particular attention will be given to the relationship between chemical formula, three-dimensional structure and chemical-physical properties (solubility, boiling point, color etc.) of organic molecules. The student will analyse the main transformations of organic compounds (acid-base reactions, ox-red, hydrolysis, etc.) necessary to understand the behaviour of the natural components of food. Theme n°1. The organic compounds: structure, isomerism, compact formula, functional groups. Nomenclature of organic compounds. Alkanes: structure, isomerism, chemical-physical proprieties, combustion reaction. Conformational analysis of alkanes and cycloalkanes, geometric isomerism in the disubstituted cycloalkanes. Alkenes: structure, chemical-physical properties, geometric isomerism. Polyenes, terpenes (short account). Electophilic adddition reactions of alkenes. Mechanism. Reactions of oxidation. Reactions of polymerization, properties and applications of polymers. Benzene and aromatic compounds: structure, nomenclature. Theme n°2 . Alcohols: structure, properties, natural sources and importance in food chemistry, acidity, oxidation to carbonylic compounds. Alkyl halides of hydrocarbons: structure, properties, reactivity with nucleofilic reagents, short account to the ecological problems (pesticides, halogenated compounds, dioxins, PCB). Phenols: structure, acidity; poliphenols, flavonoids, tannins. Use of poliphenols as anti-oxidants in food. Theme n°3 . Chirality and optical activity, absolute and relative configuration. Enantiomers, diasteroisomers and racemic mixtures. Relationship between biological proprieties and optically active compounds. Aldehydes and ketones: structure, properties, redox and nucleophic addition reactions. Semiacetals, acetals and hydrated derivative of aldehydes and ketones. Some typical carbonyl addition reactions of nitrogen nucleophilic reagent. Theme n°4 . Carbohydrates: mono-, di- and polysaccharides. Monosaccharides: structure and Fischer projections, stereochemistry. Cyclic structure and mutarotation. Disaccharides and polysaccharides: proprieties and importance in biological system. Theme n°5 . Carboxylic acids: structure, proprieties and acidity. Funcional derivatives of carboxilyc acids: acid halides, esters, amides. Reactions of nucleophilic displacements: esterification and hydrolysis of esters. Lipids: fatty acids, triglycerids, phospholipids. Natural and synthetic soaps and tensioactives. Steroids and liposoluble vitamins. Amines: structure, properties, basicity. Natural nitrogen containing compounds (alkaloids). Aminoacids and peptides: structure, acid-base properties, PI. Biologically important aminoacids. Structure of DNA (short account). Practices: Practices in laboratory: fundamental techniques for identification, separation and purification of organic compounds. Distillation, column chromatography and thin layer chromatography, extraction from aqueous solutions at different pH. Exercises on topics covered in class.