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.

Furthermore, in reference to the so-called Dublin Descriptors, this course helps to acquire the following skills:

D1 - Knowledge and understanding: The students will have to demonstrate their mastery of basic knowledge about the organic chemistry. In particular, the students must show their ability to rationalize property-structure correlations of organic molecules

D2 - Ability to apply knowledge: The students will have to show knowledge and understanding of organic reactions required to produce synthetic processes of relatively complex molecules.

D3 - Autonomy of judgment: The students will have to apply their knowledge, understanding and skills. Particularly, the students must show his ability to critical reasoning and their ability to identify the most appropriate chemical reactions aimed to the synthesis of organic molecules.

D4 - Communication skills: The students must be able to communicate clearly with a correct property of language and terminological rigor their conclusions.

D5- Learning skills: The students will have to develop learning skills that will enable them to continue studying in a self-directed or autonomous way.

The teaching will take place through the discussion of the various topics reported in the program and will include days dedicated to the clarification of doubts and the simulation of the oral exam.Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes with respect to previous statements, in line with the programme planned and outlined in the syllabus. Learning assessment may also be carried out on line, should the conditions require it.

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.

SYNTHETIC STRATEGIES FOR MACROCYCLIC BUILDING BLOCKS

Corona ethers, lariat corona ethers, cyclophanes, cryptands, metacyclophanes in 1,3-alternate conformation, calixarenes, heterocalixarenes, resorcarenes, hexameric capsules, immobilization via intrabridging, cavitands, carcerands and hemicarcerands), cyclodextrins, pseudorotaxanes. 'One-pot' synthesis and 'convergent' synthesis of calixarenes.

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.