Ateneo - UPO

frontal study of the main non-ionic reactions, with hints of process development and protecting groups. From a practical point of view, the main safety standards of an organic synthesis laboratory and the main laboratory techniques will be introduced. Introduction to the characterization of final products

Clayden, J et al.. Organic Chemistry, Oxford University Press, 2012.
Norman, Coxon. Sintesi Organica, Piccin, 1999.
La chimica organica in laboratorio - Tomo I - M. d’Ischia - Piccin
Chimica organica sperimentale - R.M. Roberts - Zanichelli
Vogel’s textbook of practical organic chemistry - A. I. Vogel – Longman
Practical process research and development - N. G. Anderson – Academic Press

Provide students with instruments to critically tackle complex molecules and reaction mechanisms.
Introduction to the main laboratory techniques in order to prepare the student to be autonomous in an organic synthesis laboratory so that he can face and solve the problems he will face in total safety

General and inorganic chemistry
Organic chemistry II
Heterocyclic chemistry
Spectroscopic Methods in Organic Chemistry

Lectures and exercises accompanied by practical experience in the laboratory

Supporting material to the course will be added to the DIR platform

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Forse cercavi: Test scritto ed esame orale e valutazione dell'attività laboratoriale

70 / 5.000
Risultati della traduzione
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Written test and oral exam and laboratory activity evaluation

1. Reactions mediated by transition metals
1. 18-electrons rule, classification of ligands and nature of the coordinative bond
2. General mechanistic considerations
3. Hydroformylation and metathesis
4. Coupling reactions and Heck reaction
5. Exercises and problem-solving activities
6. Exercises and problem-solving activities
7. Exercises and problem-solving activities
8. Exercises and problem-solving activities

2.Pericyclic reactions
1. Introduction and selection rules
2. Cycloaddition reactions and structure-reactivity relationships in dienic synthesis
3. Dipolar cycloadditions
4. Electrocyclic reactions
5. Sigmatropic reactions
6. Application to industrial syntheses (vitamin D, citral)
7. Exercises and problem-solving activities
8. Exercises and problem-solving activities

3.Carbohydrates
1. Representation and semiacetal formation
2. Anomeric effect and introduction to hyperconjugation
3. Protection reactions
4. Glycosidation reactions
5. Redox reactions
6. Application to industrial syntheses (Reichstein synthesis of vitamin C)
7. Solid-phase oligonucleotide synthesis
8. Exercises and problem-solving activities

4. Amino acids and peptides
1. Acid-basic properties of proteinogenic amino acids and their general synthesis
2. Asymmetric synthesis of amino acids
3. Solution peptide synthesis
4. Solid state peptide synthesis and introduction to polymer chemistry
5. Polymerization reactions
6. Application to industrial syntheses (Monsanto synthesis of L-DOPA)
7. Exercises and problem-solving activities
8. Exercises and problem-solving activities

5. Secondary metabolites
1. Isoprenoids and non-classic carbocations
2. Application to industrial syntheses (carotenoids)
3. Application to industrial syntheses (steroid syntheses)
4. Alkaloids
5. Multicomponent reactions (Mannich, Ugi, Passerini)Aymmetric dihydroxylation
7. Quinones
8. Exercises and problem-solving activities

6a. Stereoelectronic effects
1. General introduction
2. Application to conformational effects
3. Application to configurational effects
4. Exercises and problem-solving activities

6b. Organic photochemistry
1. General aspects
2. Synthetic uses
3. Photocycloadditions and their biological relevance
4. Exercises and problem-solving activities

7. Biological mechanisms
1. Benzoinic reaction and vitamin B1
2. Vitamin K
3. Electron-transfer reactions
4. Diotopic reactions and vitamin B12
5. Redox reactions and half-bonds
6. Exercises and problem-solving activities
7. Exercises and problem-solving activities
8. Exercises and problem-solving activities

8. protecting groups of the main functional groups
The significance of organic synthesis.
Safe working in a chemical laboratory. Contact with chemical reagents for ingestion, inhalation, direct absorption. Toxic, cancerogenic, teratogenic, flammable, explosive reagents.
Equipments.
Solvents. The effect of the solvent on chemical reactions. Selection, purification and drying of solvents.
The reagents. Purification. Measurement.
Inert atmosphere techniques.
Conducting the reaction itself. Temperature control. How to heat and cool reactions. Reactions with gas reagents. Special reaction techniques. Catalytic hydrogenation. Reactions with liquid ammonia.
Following the reaction. Thin layer chromatography (TLC).
Working up reactions. Quenching. Extraction. Drying organic solutions. Filtration. Evaporation of the solvent.
Purification processes. Column chromatography. Distillation. Crystallization. Sublimation.
Product characterization.
The research notebook.
Examples of reaction procedures: how to make calculations and choose the right apparatus.
Searching the literature.
Non-conventional techniques. Green chemistry. Phase transfer catalysis. Microwaves. Ultrasonication. Biocatalysis. Flow chemistry.
Industrial organic synthesis. Properties of an industrial synthesis. Process chemistry: laboratory synthesis, scale up, pilot plant, production. Conducting the reaction, work up and purification at industrial level.

Capacity to address the chemistry and the synthesis of complex molecules applying modern reaction mechanisms

From a practical point of view, the student at the end of the course will be able to search for a chemical reaction in the scientific literature, read the experimental procedure, set up the calculations for the preparation of the chemical reaction, set it up working safely, choosing the right equipment / glassware, using the most appropriate techniques (of which he will know the operating principles), monitor the reaction, isolate the product and purify it. He will also have learned the differences between a small-scale synthesis and a large-scale synthesis.