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

Spectroscopic Methods in Organic Chemistry: Knowledge of the most important spectroscopic techniques (mainly IR and NMR) for the determination and characterization of organic molecules. The elaboration of the obtained data allows to intervene in the synthesis and analysis of the organic substances considered.

Lectures for the advanced organic chemistry module. For the PESF module The course consists of three parts.
The first part concerns a series of lectures focused on safety and on the main synthesis techniques in an organic synthesis laboratory. At the end of this part, students are provided with reaction procedures from scientific articles, which are translated and analyzed on the blackboard.
The second part consists of the laboratory, where the students will practice a series of reactions.
The third part of lectures concerns the search for information in scientific literature, some unconventional synthesis techniques and industrial synthesis. One of these lessons is held in the computer room where students have the opportunity to search for information in the scientific literature through the use of databases, search engines and sci-finders.
The frontal lessons are held with the support of power point slides that are provided to students at the beginning of the course.
Optional seminars held by external speakers are also offered every year.

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

For the advanced organic chemistry module Written test with oral presentation on a topic chosen by the student.
For the PESF module Access to the laboratory is preceded by a first test with 28 questions. 22 questions concern the topics covered in the preparatory lessons for the laboratory. In fact, the student must demonstrate knowledge of the prerequisites for working in safety, as well as the basic techniques that he will use in the laboratory. 6 questions instead concern the resolution of exercises and questions relating to a synthetic procedure in English taken from the scientific literature. In order to achieve the sufficiency, the student must answer at least 16 questions correctly. During the course of the laboratory, the student is evaluated during the various experiments based on the commitment and the results obtained.
A second test of 5 questions concerns the topics covered after the laboratory, such as the search for information in scientific literature, unconventional synthesis techniques and synthesis in industry. To achieve sufficiency, the student must answer at least 3 out of 5 questions correctly.
The final grade will take into account both the written tests and the activity carried out in the laboratory.

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.
Hazard statements, precautionary statements.
Contact with chemical reagents for ingestion, inhalation, direct absorption. How to behave in case of poisoning.
Toxic, cancerogenic, teratogenic, flammable, explosive substances.
How to dispose of chemical waste. Physical risks.
Equipments.
Solvents. The effect of the solvent on chemical reactions. Selection, purification and
drying of solvents.
The reagents. Purification. Measurement.
Inert atmosphere techniques.
Set up different types of reactions. Temperature control. How to heat and cool reactions. Reactions with gas reagents. Shifting the reaction equilibrium. 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 (simple, fractional, vacuum, steam). 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. Microwave. Biocatalysis. Flow chemistry. Electrochemistry. Photochemistry.
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.