Chemical sciences
Study-unit Code
Chimica organica
Stefano Santoro
  • Stefano Santoro
  • 42 ore - Stefano Santoro
Course Regulation
Coorte 2022
Learning activities
Discipline chimiche organiche
Academic discipline
Type of study-unit
Obbligatorio (Required)
Type of learning activities
Attività formativa monodisciplinare
Language of instruction
Frontier molecular orbital theory in modern organic chemistry. Fundamental concepts on chemical reactivity. Thermal and photochemical pericyclic reactions. Main chemical processes based on the use of organometallic reagents or catalyzed by transition metal complexes and their applications in organic synthesis.
Reference texts
Slides used during the lectures will be provided in electronic format.
Educational objectives
Aim of this course is to provide an advanced, albeit qualitative, understanding of the main concepts underlying organic chemical reactivity, especially in terms of molecular orbital theory. The application of this theory is mainly directed towards the study of pericyclic reactions. Moreover, a large part of the course deals with the study of reactivity of organometallic compounds, of selected transition metals catalyzed reactions and their applications in organic synthesis.
Main knowledge acquired will be:
- qualitative theoretical knowledge of molecular orbital theory;
- theoretical knowledge on chemical bonding and general chemical reactivity;
- theoretical knowledge on frontier molecular orbital theory;
- knowledge on the application of frontier molecular orbital theory on thermal and photochemical pericyclic reactions;
- knowledge on properties and reactivity of the main classes of organometallic compounds and their applications in organic synthesis;
- knowledge on the applications of transition metals complexes in organic synthesis;
- knowledge on fundamental concepts in modern organic synthesis.
The main competence (i.e. the ability to apply acquired knowledge) will be:
- being able to design an organic chemical reaction;
- ability to solve problems in chemical synthesis;
- design multi-step organic syntheses.
In order to be able to understand the topics of the course you must have successfully passed the Chimica Organica 1 and Chimica Organica 2 exams.
Teaching methods
The course is delivered through lectures, held in the classroom, on all the topics object of the course. Moreover, there will be sessions of exercises solving in the classroom, aimed at developing skills in planning organic reactions and multi-step syntheses.
Other information
Learning verification modality
The exam consists in an oral test of about 40 minutes. The test is aimed at the assessment of the level of understanding of theoretical basis of chemical reactivity and of the ability to apply the acquired knowledge on the design of chemical syntheses. The overall evaluation of the exam is based on the following aspects: completeness and correctness of the answers, ability to elaborate and connect concepts, ability to correctly organize the exposure of the topics. These aspects will have the following weight, respectively, on the final evaluation: 60%, 20%, 20%.
Extended program
Molecular orbital theory. Frontier molecular orbital theory. HOMO, LUMO and SOMO frontier molecular orbitals. The concept of reaction coordinate. Fundamental concepts in chemical reactivity: basicity and nucleophilicity, acidity and electrophilicity, hard and soft nucleophiles and electrophiles. Thermal pericyclic reactions. Woodward-Hoffmann rules. 1,3-dipolar cycloadditions, cheletropic reactions; sigmatropic rearrangements: Cope rearrangement, 1,3-sigmatropic rearrangement, Claisen rearrangement and their applications in organic synthesis. Electrocyclic reactions. Diels-Alder reaction: reactivity and selectivity. 1,3-dipolar reactions. Photochemical pericyclic reactions. Woodward-Hoffmann rules for photochemical pericyclic reactions. Photochemical cycloadditions, sigmatropic rearrangements and electrocyclic reactions.
Organometallic compounds of lithium, magnesium, zinc, tin: structure, preparation and reactivity. Hydrogen/metal, halogen/metal and metal/metal exchange reactions and their application in organic synthesis. Organocopper compounds: structure, preparation and applications in organic synthesis.
Organometallic compounds of transition metals: general theory, Dewar-Chatt-Duncanson model, 18-electrons rule, ligands classification. Structural features and preparation of transition metals complexes. Fundamental processes involving transition metals complexes; the catalytic cycle. Cross-coupling reactions. Application of transition metals in the activation of unsaturated organic compounds. Application of metal-carbenes obtained from diazo-compounds. Metallo-carbenes and the metathesis reaction. Palladium-catalyzed reactions on allylic substrates; Tsuji-Trost reaction. Pauson-Khand reaction. C-H activation reactions on aromatic compounds; directing groups and regioselectivity. Strategies for meta- and para-selectivities. Introduction to the C-H activation of sp3 carbons. Synthetic applications.
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