Ateneo - UPO

The significance of organic synthesis.
Safe working in a chemical laboratory.
Equipments.
Reaction solvent.
The reagents.
Inert atmosphere techniques.
Setting up the reaction.
Following the reaction.
Working up reactions.
Purification processes.
Product characterization.
The research notebook.
Examples of synthetic procedures.
Searching in the literature.
Non-conventional synthetic techniques.
Process chemistry.

Vogel’s textbook of practical organic chemistry - A. I. Vogel – Longman

Practical process research and development - N. G. Anderson – Academic Press

Pratical Organic Synthesis - A student’s guide - R. Keese; M.P. Brandle; T.P. Toube

Advanced pratical organic chemistry – John Leonard; Barry Lygo; Garry Procter

The aim of this course is to introduce the student to the practical organic synthesis. It consists of a series of lessons 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 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; he/she will also be able to understand a procedure for setting up a reaction taken from scientific literature, evaluate it critically and apply its knowledge and understanding by reproducing this reaction in the laboratory. Last, the student will be able to communicate his/her 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 in divided in three parts.
The first part consists in frontal lessons that regard the safe working in a chemical laboratory and the main techniques used in an organic chemistry laboratory. At the end of this section, procedures of reactions taken from scientific papers are given to the students, translated and analysed at the blackboard.
The second section is the laboratory, where the students practice with 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 searching the literature, non-conventional techniques and process chemistry are handled. One of these lessons is given in the computer room, where the students have the opportunity to search information in the scientific literature using data bases, search engines and Sci-Finder.
The frontal lessons are given with the support of power point slides, which are furnished to the students at the beginning of the course.
Every year a couple of seminars given by guest lecturers are proposed.

The student will give a written test with 28 questions before attending the laboratory. 22 questions concern the topics handled in the frontal lessons and the student has to demonstrate that he/she knows all the safety rules and the main techniques that he/she 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 his/her 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 techniques 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 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.

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 in safe conditions; choose the right apparatus/glassware; use the most appropriate synthetic technique; follow the reaction; isolate the product and purify it. The student will also know the main differences between a small-scale and large-scale synthesis.