SINTESI E MECCANISMI DI REAZIONE IN CHIMICA ORGANICA

The course aims to deepen the basic knowledge of organic chemistry. The most common synthetic strategies of asymmetric synthesis and their reaction mechanisms will also be analyzed in detail. In this course the student will learn the basic concepts of "green chemistry" with references to organic reactions that are sustainable from an environmental and economic point of view

Lectures

RADICALS

Radical stability - Halogenation in alkanes - Probability and reactivity in product formation - principle of reactivity-selectivity - Peroxide formation - Addition of radicals to alkenes - Stereochemistry of radical substitution and addition reactions - Radical substitution of allyl and benzyl hydrogens - radical reactions in biological systems.

ORGANOMETALLIC COMPOUNDS AND FORMATION OF NEW C-C BONDS

Organolithium and organomagnesium compounds - Transmetallation - Organocuprates - Palladium-catalyzed coupling reactions - Formation of new C-C bonds: Suzuki, Stille, Heck, Sonogashira, Negishi. Formation of new C = C bonds: Metathesis; Click Chemistry.

CATALYSIS IN ORGANIC REACTIONS AND IN ENZYMATIC REACTIONS

Catalysis in organic reactions - Acid, basic, nucleophilic catalysis with metal ions - Intramolecular catalysis - Catalysis in biological reactions - Acid/base catalysed enzymatic reaction of hydrolysis of amides - Enzymatic reaction of enediolic transposition - Enzymatic reaction of a retroaldo-reaction

ASYMMETRIC SYNTHESIS

Introduction and principles - Addition to carbonyl compounds - a-substitution with chiral enolates - Asymmetric aldolic reactions - Addition to double bonds C-C - Reduction and oxidation - Transpositions - Hydrolysis and esterification

GREEN CHEMISTRY

Definition of green chemistry - The 12 principles of green chemistry - The atom economy and the other parameters to evaluate the efficiency of a process - The use of solvents in chemical processes - Limitations, regulations and dangers of the different classes of solvents - Metals heavy, definition, uses and regulations - Polyurethanes, isocyanates and phosgene, sustainable alternatives to phosgene - Dangerous methyl isocyanate and environmental disasters - PAHs, dioxins and furans: structures, chemical-physical characteristics and toxicology and ecotoxicology of these substances - Raw materials for a sustainable industry: terpene polymers, PLA, biofuels and biodiesel

1) Notes from lessons

2) P. Y. BRUICE - Chimica organica - 3a Edizione EdiSES

3) W.H. BROWN e altri autori - Chimica Organica 5a Edizione EdiSES

4) STUART WARREN “Designing Organic Syntheses”, John Wiley &Sons

5) GARRY PROCTER “Sintesi Asimmetrica”, Edizione EdiSES

6) PAUL ANASTAS and JOHN WARN “Green chemistry theory and practice - Oxford University Press Inc.