Unit ORGANIC CHEMISTRY 3
- Course
- Chemical sciences
- Study-unit Code
- GP004029
- Curriculum
- Chimica organica
- Teacher
- Luigi Vaccaro
- CFU
- 12
- Course Regulation
- Coorte 2020
- Offered
- 2020/21
- Type of study-unit
- Obbligatorio (Required)
- Type of learning activities
- Attività formativa integrata
CATALYSIS IN ORGANIC CHEMISTRY
| Code | GP004041 |
|---|---|
| CFU | 6 |
| Teacher | Oriana Piermatti |
| Teachers |
|
| Hours |
|
| Learning activities | Caratterizzante |
| Area | Discipline chimiche organiche |
| Academic discipline | CHIM/06 |
| Type of study-unit | Obbligatorio (Required) |
| Language of instruction | Italian |
| Contents | Catalysis and sustainable development. Kinetic aspects of catalysis. Homogeneous catalysis with metal complexes. Metal-free homogeneous catalysis: Brønsted acids and bases, organocatalysis. Homogeneous asymmetric catalysis. Heterogeneous catalysis: catalyst recovery and recycling. Immobilization strategies of homogeneous catalyst. Comparison of the catalytic activity between different supports and comparison with the homogeneous catalyst. |
| Reference texts | 1. Teacher lectures; 2. Catalysis: Concept and Green Applications; 3. Gadi Rothenberg, Wiley WCH, 2008. 4. Recoverable and recyclable catalysts; M. Benaglia, Wiley, 2009. 5. Catalyst Immobilization: Methods and Applications; M. Benaglia, A. Puglisi; Wiley 2020 |
| Educational objectives | The aim of the course is to provide to the students the fundamental concepts of homogeneous and heterogeneous catalysis applied to organic synthesis and in particular to the asymmetric synthesis. The main acquired knowledge regarding the use of metal catalysts with chiral ligands, organic catalysts, acid-basic catalysts in the main fundamental organic processes such as the aldol addition reaction, the Mannich reaction, the Michael reaction, the Diels-Alder reaction, epoxidation and reduction reactions. At the end of the course the student should be able to analyze and rationalize the effect of a catalyst on both the reactivity and regio- and diastereoselectivity of the organic process. |
| Prerequisites | In order to effectively follow the course of Organic Chemistry 3 is necessary to know the contents of Organic Chemistry 1 and Organic Chemistry 2 of the Bachelor of Chemistry. |
| Teaching methods | The course is organized as follows: -Lectures on all the subject of the course with examples of recent literature. -An exercise in which students research an example of the recent literature on metal or organic catalysis in homogeneous or heterogeneous phase and presentation of the article to colleagues of the course. |
| Other information | no |
| Learning verification modality | An oral exam aimed at ascertaining the level of knowledge about the different types of catalysis applied to fundamental processes in organic synthesis. The examination consists of a discussion of about 30-40 minute of 2-3 questions with closed stimulus and open answer. |
| Extended program | Fundamental aspects of catalysis: replacyng stoichiometric reaction with a catalytic cycle. Sustainable development, environmental impact. Kinetic aspects of catalysis. The reaction profile and the reaction coordinate: pre-equilibrium, catalyst precursor and active catalyst. Basic concepts in catalysis: catalyst/substrate interaction, the catalyst deactivation, inhibition, and poisoning. Turnover number (TOF) and turnover frequency (TOF). Homogeneous catalysis with metal complexes. Exchange of ligands, dissociation and coordination. Metal-free homogeneous catalysis: Brønsted acids and bases, organocatalysis. Noncovalent organocatalysis: hydrogen bond. Covalent organocatalysis: formation of enamines. Use of water as reaction medium in homogeneous catalysis with metal complexes and organocatalysts. Homogeneous asymmetric catalysis. Application to the main classes of organic reactions: carbon-carbon bond formation (aldol condensation, Michael, Mannich, Diels-Alder), oxidations and reductions. Advantages and disadvantages of homogeneous catalysis. Heterogeneous catalysis: catalyst recovery and recycling. The concept of the active site. Langmuir-Hinshelwood model for heterogeneous catalysis. The solid supports: organic, inorganic, hybrid organic-inorganic materials. The choice of support: specific surface area, accessibility of substrate, stability. Supported chiral catalysts on insoluble matrices. Immobilization strategies of homogeneous catalysts: adsorption, encapsulation, covalent bonding, electrostatic interaction, self-assembly. Comparison of the catalytic activity for some of the most common chiral ligands: homogeneous vs. heterogeneous catalyst and for the heterogeneous catalysts between the different supports. Metal nanoparticles catalysis. |
ORGANIC SYNTHESIS
| Code | GP004040 |
|---|---|
| CFU | 6 |
| Teacher | Luigi Vaccaro |
| Teachers |
|
| Hours |
|
| Learning activities | Caratterizzante |
| Area | Discipline chimiche organiche |
| Academic discipline | CHIM/06 |
| Type of study-unit | Obbligatorio (Required) |
| Language of instruction | Italian |
| Contents | The course deals with the most common methods of synthetic methodologies used to understand the reactivity of organic molecules and to design the synthesis of commonly used molecules both in academic and industrial |
| Reference texts | Those attending will be provided, electronically, with the same material used by the lecturer for classroom lessons. A representative text of reference is: Advanced Organic Chemistry, 2007 Ed AUTHORS: Carey, Francis A., Sundberg, Richard J. Part A: Structure and Mechanisms Part B: Reaction and Synthesis |
| Educational objectives | The course should demonstrate to the student the importance of the fundamental synthetic methodologies to understand the reactivity of organic molecules and to design the synthesis of commonly used molecules both in academic and industrial The course should allow the student to acquire the following basic knowledge: Know stereoselectivity in reactions Understand the fundamental methods of oxidation of organic molecules Know the basic methods of reducing the organic molecules Know the fundamental chemistry of carbanions and organometallic reagents Know the key processes used in modern production such as enantioselective oxidations and methodologies for process optimization |
| Prerequisites | Knowledge of basic organic chemical elements is required (Organic Chemistry I and II). |
| Teaching methods | The course provides theoretical frontal lessons and practical examples, to facilitate the student in learning modern techniques of chemical process optimization. In the lessons of 2 hours each, held in the classroom, the principles of Organic Synthesis will be illustrated and some chemical issues will also be introduced to better understand the practical examples. |
| Learning verification modality | The proof of profit includes the assessment of written reports on laboratory activities and an oral test, which will involve the formulation of 4-5 questions over a period of approximately 40 minutes. The test is aimed at assessing students' abilities and assessing the environmental impact of a chemical process and distinguishing the various factors that influence it. The overall evaluation of the exam will take into account the following aspects: correctness and adequacy of responses, processing skills and conceptual connection, mastery and language skills, according to the following percentages: 60%, 20%, 20%. |
| Extended program | The course includes theoretical frontal lessons - Stereoselectivity in nucleophilic addition reactions to carbonyl functionality. Rule of Cram, Karabatos, Felkin, Felkin-Anh - Oxidation reactions (oxidation of various organic functions). - Reduction reactions (reduction of various organic features). - Carbanions in organic synthesis. - Notes on organometallic compounds and their reactions - Synthesis of Sertralin - Synthesis of Talampanel - Synthesis of Swainsonines - Synthesis of Indinavir |