Ateneo - UPO

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.

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

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.

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.

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.

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.

The significance of organic synthesis. Safe work practices 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. Laboratory equipment. Glassware. The solvent of reaction. The effect of the solvent on chemical reactions. Selection, purification and drying of solvents. The reagents. Purification. Measurement.
Inert atmosphere techniques. Set up of different types of reactions. Temperature control. How to heat and cool reactions. Reactions with gas reagents. Shifting the reaction equilibrium. Catalytic hydrogenation. Following the reaction. Thin layer chromatography (TLC). Performing reaction work-up. Quenching. Extraction. Drying organic solutions. Filtration. Evaporation of the solvent. Purification processes. Column chromatography. Distillation (simple, fractional, vacuum, steam). Crystallization. Sublimation. Product characterization.
The laboratory notebook. Examples of different synthetic procedures: how to make calculations and choose the right apparatus/glassware.
Searching the literature. Non-conventional methods of synthesis. Green chemistry. Phase transfer catalysis. Microwave-assisted synthesis. Biocatalysis. Flow chemistry. Electrochemistry. Photochemistry. Industrial synthesis. Characteristics of an industrial synthetic route. Process development: laboratory synthesis, scale-up, pilot plant, production. Setting up the reaction, performing reaction work-up, and purifying the product in an industrial setting.

The student at the end of the course will be able to: search the scientific literature; find out the desired reaction; read and understand the corresponding experimental procedure; make the calculations for determining the amounts of solvents and reagents; conducting the reaction under safe conditions; choose the right apparatus/glassware; use the most appropriate synthetic techniques; follow the reaction; isolate the product, purify it and characterize it through spectroscopic methods (NMR) as well as melting point. The student will also learn the differences between small-scale and large-scale synthesis.