SYNTHESIS AND REACTION MECHANISMS IN ORGANIC CHEMISTRY

The course aims to deepen the basic knowledge of covalent and supramolecular organic chemistry. The most common synthetic strategies of asymmetric synthesis and their reaction mechanisms will also be analyzed in detail.

With reference to the so-called Dublin Descriptors, the learning outcomes of the course are:

D1 - Knowledge and understanding - The student must demonstrate mastery of the basic knowledge related to organic chemistry. The student must rationalize the property-structure correlations; in particular, he/she must be able to recognize the functional groups of organic molecules, their main physical properties and understand their chemical behavior

D2 - Ability to apply knowledge and understanding - The student must be able to apply the knowledge acquired in an appropriate and flexible way in order to develop, by adopting chemical symbols, the synthesis reactions of relatively complex organic molecules

D3 - Autonomy of judgment - The student must demonstrate critical reasoning skills and, through the knowledge acquired during the course, must schematically and appropriately identify the most suitable solutions for the synthesis of organic molecules

D4 - Communication skills - The student must be able to communicate clearly and with an adequate and rigorous chemical language the notions acquired during the course.

D5 - Learning ability - The student must demonstrate that he/she has developed good learning and in-depth skills on the topics of the course in order to easily face the subsequent study paths.

Information for students with disabilities and/or DSA

To ensure equal opportunities and in compliance with current laws, interested students can request a personal interview in order to plan any compensatory and/or dispensatory measures, based on educational objectives and specific needs.

FRONTAL LESSONS (6 CFU)

The teaching will be carried out through the treatment of the various topics reported in the program and will include days dedicated to clarifying doubts and simulating the oral exam to be taken. If the teaching is taught in mixed mode or remotely, the necessary changes may be introduced with respect to what was previously declared, in order to respect the expected program and reported in the syllabus.

RADICALS

Stability of radicals – Halogenation in alkanes – Probability and reactivity in the formation of products – principle of reactivity-selectivity – Formation of peroxides – Addition of radicals to alkenes – Stereochemistry of radical substitution and addition reactions – Radical substitution of allylic and benzylic hydrogens – radical reactions in biological systems.

SYNTHETIC STRATEGIES FOR THE OBTAINMENT OF MACROCYCLIC BUILDING BLOCKS

Crown ethers, lariat crown ethers, cyclophane cryptands, metacyclophanes in 1,3-alternate conformation, calixarenes, heterocalixarenes, resorcarenes (synthesis, limiting conformations, 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 aldol reactions – Addition to C-C double bonds – Reduction and oxidation – Rearrangements – Hydrolysis and esterification

1) lecture notes

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