Ateneo - UPO

frontal study of the main non-ionic reactions, with hints of process development and protecting groups. Synthetic organic chemistry.
Safety in a chemical laboratory.
Laboratory equipment and glassware.
Reaction solvent: the role and choice.
The reagents.
Inert atmosphere techniques.
Setting up the reaction.
Following the reaction.
Performing reaction work-ups.
Purification processes.
Product characterization.
The laboratory notebook.
Examples of synthetic procedures.
Searching in the literature.
Non-conventional synthetic techniques.
Process chemistry.

Clayden, J et al.. Organic Chemistry, Oxford University Press, 2012.
Norman, Coxon. Sintesi Organica, Piccin, 1999.
Vogel’s textbook of practical organic chemistry, 5th Edition –
B. S. Furniss; A. J. Hannaford; P. W. G. Smith; A. R. Tatchell

Advanced practical organic chemistry –
J. Leonard; B. Lygo; G. Procter
Laboratory Techniques in Organic Chemistry: Supporting Inquiry-driven Experiments - Brossura, 4th Edition –
J. R. Mohrig; D. G. Alberg; G. E. Hofmeister; P. F. Schatz; C. N. Hammond
Practical process research and development - N. G. Anderson – Academic Press

Provide students with instruments to critically tackle complex molecules and reaction mechanisms.
The aim of this course is to introduce the student to the practical organic synthesis. It consists of a series of lecturers focused on the safety in laboratory and the main techniques used for the set up and control of the reaction, together with the purification of the reaction product. All these methods are carried out in a series of practical experiments during the laboratory. Moreover, some aspects regarding the scientific literature search and process chemistry will be addressed. At the end of the course, the student will know how to work in a safe manner and will know the main techniques used in an organic synthesis laboratory; she/he will also be able to understand a procedure for setting up a reaction taken from scientific literature, evaluate it critically and apply her/his knowledge and understanding by reproducing this reaction in the laboratory. Last, the student will be able to communicate her/his knowledge and understanding in the laboratory with the colleagues and the professor. The course will allow the student to gain the necessary judicial autonomy to work in a safe manner, to conduct an organic synthesis in the laboratory, and to search information in the scientific literature.

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. The course is divided into three parts.
The first part consists of lectures that cover safe practices in a chemical laboratory and the main techniques used in an organic chemistry laboratory. At the end of this section, students are given reaction procedures from scientific papers, which are translated and analysed on the blackboard.
The second part is the laboratory section, where students practice a series of reactions using the techniques learned in the first part of the course.
In the third part of the course, aspects such as literature searching, non-conventional techniques of synthesis, and process chemistry are covered. One of these lessons takes place in the computer room, where students have the opportunity to search for information in the scientific literature using databases, search engines, and SciFinder.
The lectures are supported by PowerPoint slides, which are provided to the students at the beginning of the course. Every year, a couple of seminars are given by guest lecturers.

Supporting material to the course will be added to the DIR platform
Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/services- students physical-or-learning-disabilities
Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects

For the advanced organic chemistry module Written test with oral presentation on a topic chosen by the student.
The student will give a written test with 28 questions before attending the laboratory. 22 questions concern the topics handled in the frontal lecturers and the student has to demonstrate that she/he knows all the safety rules and the main techniques that she/he will apply in the laboratory. 6 questions consist in answering questions and solving exercises that regard a procedure in English taken from a scientific paper. In order to pass this test, the student should answer correctly to at least 16 questions.
During the laboratory the student will be evaluated taking into account her/his commitment and the results gained.
A second written test of 5 questions at the end of the course will regard the last topics of the course, such as searching the literature, non-conventional methods in organic synthesis and process chemistry. In order to pass this test, the student should answer correctly to at least 3 questions over the 5 given.
The final mark will take into account the results of the two written tests and of the laboratory activities.

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.