Ateneo - UPO

Synthetic organic chemistry. Safety in a chemical laboratory. Laboratory equipment and glassware. Reaction solvent: role and selection. Reagents. Working under Inert/Anhydrous Conditions (Various Techniques). Setting up a reaction. Monitoring the reaction. Performing reaction work-up procedures. Purification of the reaction product. Product characterization. The laboratory notebook. Examples of synthetic procedures. Searching scientific literature. Non-conventional synthetic techniques. Process chemistry and industrial synthesis.

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 practical organic synthesis. It is structured as a series of lecturers focused on the laboratory safety and the main techniques for setting up reactions, minitoring reactions, and purifying reaction products. These techniques will then be put into practice through a series of laboratory exercises. Moreover, some aspects regarding the scientific literature search and process chemistry will be addressed. In the final part of the course, some aspects related to searching for information in the scientific literature, process chemistry, and synthesis in the chemical and pharmaceutical industry will be covered. At the end of the course, students will have learned how to work safely in an organic synthesis laboratory and will be familiar with the main techniques of practical synthesis. They will also be able to understand a procedure for setting up a reaction taken from the scientific literature, critically evaluate it, and reproduce it in the laboratory. Finally, they will be able to effectively communicate the results obtained and discuss them with their peers and with the Professor during laboratory activities. The course will provide students with the critical judgment and autonomy necessary to work safely in an organic/pharmaceutical chemistry laboratory, to set up organic synthesis reactions, and to conduct critical research in the scientific literature.

Knowledge of the most important spectroscopic techniques (primarily IR and NMR) for the identification and characterization of organic molecules. The interpretation of the obtained data enables intervention in the synthesis and analysis of the organic compounds under study.

The course is divided into three parts. The first part consists of a series of lectures focused on safety and the main synthetic techniques used in an organic synthesis laboratory. At the end of this section, students are provided with reaction procedures taken from scientific articles, which are translated and analyzed on the board. The second part is dedicated to laboratory exercises, where students will carry out a series of reactions, applying the techniques they have learned. The third part includes additional lectures focused on searching for information in the scientific literature, as well as exploring some non-conventional synthetic techniques and industrial synthesis. One of these lectures takes place in the computer laboratory/room, where students have the opportunity to search for scientific information using databases, specialized search engines and SciFinder. The lectures are supported by PowerPoint slides, which are made available to the students. Every year, an optional seminar is offered, held by an external speaker, and a guided visit is organized to a company involved in the development, production, and sale of Active Pharmaceutical Ingredients (APIs) and related services for the pharmaceutical industry.

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 take a written test consisting of 28 questions before attending the laboratory. 22 questions will cover the topics discussed during the first part of the course, and the student must demonstrate knowledge of all the safety rules and the main techniques that will be applied in the laboratory. 6 questions will involve answering and solving exercises based on a procedure in English taken from a scientific paper. To pass this test, the student must correctly answer at least 16 questions. During the laboratory sessions, the student will be assessed based on their commitment and the results obtained. A second written test, consisting of 5 questions, will be administered at the end of the course. This test will focus on the final topics of the course. To pass this test, the student must correctly answer at least 3 out of the 5 questions. The final mark will be based on the results of the two written tests and performance during the laboratory activities.

The meaning of organic synthesis. Safety in a synthesis laboratory. Safety rules. R and S phrases, H and P statements, and hazard symbols. Exposure to chemicals by ingestion, inhalation, and skin absorption. How to behave in case of poisoning. Toxic, carcinogenic, flammable, and explosive substances. Disposal of chemical waste. Physical hazards. Glassware and non-glass equipment. The reaction solvent. Influence of the solvent on reactions. Purification and drying of solvents. Reagents. Working under anhydrous conditions: various drying and degassing techniques. Heating and cooling reactions. Reactions involving gases. Shifting the reaction equilibrium. Catalytic hydrogenation. Monitoring a reaction. Thin Layer Chromatography (TLC). Working up reactions. Quenching. Extraction. Examples of purification workflows. Pre-drying and drying. Filtration. Solvent evaporation. Product purification. Column chromatography. Simple, fractional, vacuum, and steam distillation. Crystallization. Characterization of the reaction product. The laboratory notebook. Examples of different synthetic procedures: how to do the calculations and choose the correct equipment/glassware. Information retrieval. Primary and secondary sources. Unconventional synthesis techniques. Green chemistry. Phase-transfer catalysis. Microwave-assisted synthesis. Biocatalysis. Flow chemistry. Photochemistry and photocatalysis. Ionic liquids. Synthesis in the pharmaceutical and chemical industry. Characteristics of an industrial synthetic route. Process development: laboratory synthesis, scale-up, pilot plant, production. Reaction setup, work-up, and product purification in industry.

At the end of the course, the student will be able to: search for a chemical reaction in the scientific literature; read and understand the experimental procedure; perform the necessary calculations to set up the organic reaction; carry out the reaction safely, choosing the appropriate equipment/glassware and applying the most suitable synthetic techniques (of which they will understand the operating principles); monitor the reaction; isolate the product, purify it, and characterize it through spectroscopic analyses (NMR and IR) and melting point determination. Moreover, the student will have learned the differences between small-scale and large-scale synthesis.