Print Course LABORATORY OF SYNTHETIC MEDICINAL CHEMISTRY Course ID F0481 Academic Year 2017/2018 Year of rule 2014/2015 Degree 1505 - CHIMICA E TECNOLOGIA FARMACEUTICHE Curriculum CORSO GENERICO Teaching leader Teachers CFU 8 Teaching duration (hours) 32 Individual study time 120 SSD CHIM/08 - CHIMICA FARMACEUTICA Course type Modulo di sola Frequenza Course category C - Affine o integrativo Year 4 Period Annuale Frequenza obbligatoria Yes Grading type Final judgment Teaching language Italian Abstract The significance of organic synthesis. Safe working in a chemical laboratory.

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The reagents. Inert atmosphere techniques. Conducting the reaction itself. Following the reaction. Working up reactions. Purification processes.

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Product characterization. The research notebook.

Searching the literature. Non-conventional techniques. Process chemistry. Reference texts 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. Vogel – Longman Practical process research and development - N. Anderson – Academic Press Teaching targets 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 apply the acquired knowledge and understanding in the laboratory, reproducing a procedure for the set up of a reaction taken from the scientific literature 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. Prerequisites Organic Chemistry 1, Drug Analysis 2 Didattics Methods 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.

Grading rules The student will give a written test with 30 questions before attending the laboratory. 25 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. 5 questions consist in answering questions and solving exercises that regard a procedure in english taken from a scientific paper. During the laboraotry 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. The final mark will take into account the results of the two written tests and of the laboratory activities. Full arguments The significance of organic synthesis. Safe working in a chemical laboratory. Contact with chemical reagents for ingestion, inhalation, direct absorption. Toxic, cancerogenic, teratogenic, flammable, explosive reagents.

The effect of the solvent on chemical reactions. Selection, purification and drying of solvents.

The reagents. Inert atmosphere techniques. Conducting the reaction itself. Temperature control.

How to heat and cool reactions. Reactions with gas reagents. Special reaction techniques. Catalytic hydrogenation.

Reactions with liquid ammonia. Following the reaction. Thin layer cromatography (TLC). Working up reactions.

Drying organic solutions. Evaporation of the solvent.

Purification processes. Column cromatography. 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.

Ionic liquids. 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. Expected learning objectives The student at the end of the course will be able to search the scientific literature, find 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 appartus/glassware, use the most appropriate synthetic tecnique, 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.

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