The aim of the course is to learn the theoretical and practical basic knowledge necessary to the preparation, purification and characterization of substances showing pharmaceutical interest and to the isolation and characterization of biological molecules from natural sources. Graduates in Chimica e Tecnologia Farmaceutiche must be aware of the basic techniques used in a synthetic laboratory as well as to acquire the dexterity necessary for the realization of safe synthesis and extraction of molecules of pharmaceutical interest. At the end of the course the student will know how to work safely in an organic synthesis laboratory, will be able to understand and reproduce the synthetic procedures described in the literature and then set up, monitor organic reactions and isolate the product in pure form.

Theoretical lessons

1. Safety in the Organic Chemistry Laboratory and recording the results.

2. TLC: uses and practical aspects of execution.

3. Design and execution of organic synthesis: the impact of various experimental parameters on the execution of organic reactions. Laboratory equipment, assembling components for carrying out typical reactions. Stirring, heating and cooling  reaction mixtures. Phase transfer catalysts. Excluding moisture from a reaction mixture, reactions under inert atmosphere.

4. Filtration techniques and filtering media. Execution and equipment.

5. Crystallization: theoretical basis, choice of the solvent, simple and fractional crystallization, optical resolution by crystallization. Decolorization and crystal drying. Execution and equipment.

6. Liquid-liquid extraction: reminders and in-depth analysis of the fundamental principles, continuous and discontinuous extraction. Equipment and evaporation of the solvent.

7. Drying of organic solvents and solutions.

8. Techniques of extraction of natural products: maceration, percolation, infusion, decoction, digestion. Supercritical fluid extraction, Accelerated Solvent Extraction (ASE) and Naviglio extractor.

9. Use of microwaves and ultrasounds in extractive processess and in organic synthesis.

10. Distillation: simple distillation, fractional distillation, vacuum distillation, azeotropic distillation and steam distillation. Theory, practical aspects and equipment.

11. Column chromatography: equipment and practical aspects.

12. Sublimation: reminders and in-depth analysis of the fundamental principles, atmospheric pressure and vacuum sublimation. Equipment and practical aspects of the technique.

The topics covered will also be explored in depth through practical and numerical exercises to aid understanding.

In order to attend the laboratory practice and acquire the frequency signature, it is necessary to have passed the exam of Organic Chemistry I and attended the laboratory practice of Drug Analysis II.

In order to take the exam it is necessary to acquire the signature of attendance and have passed the examinations of Organic Chemistry I, Drug Analysis I and Drug Analysis II.

D1 - Knowledge and understanding. The student should have acquired the basic knowledge useful for the synthesis and extraction of substances of pharmaceutical interest from both a theoretical and practical perspective. The student will be able to understand an experimental procedure concerning the synthesis, extraction and characterization of an organic compound of biological interest.

D2 - Applying knowledge and understanding. The student will be able to apply the knowledge acquired during the course, and then be able to conduct practical experiments of synthesis and extraction of substances of pharmaceutical interest, and to appropriately treat a reaction mixture to isolate and purify the desired products through the use of common laboratory procedures.

D3 - Making judgements. The student must show independence of judgment in the interpretation of the experimental data and of the obtained results, as well as the ability to plan and conduct an experiment in organic synthesis employing methods explained and implemented experimentally during the course.

D4 - Communication skills. After completing the course the student will be able to expose what he has learned using appropriate terminology for the purpose of scientific communication regarding proper methods and issues concerning the preparation and purification of compounds of pharmaceutical interest.

D5 - Learning skills. The student will have developed the learn ability useful to continuously update his knowledge and will be able to use it in order to face new synthetic and extractive challenges.

The teaching material prepared by the lecturer in addition to recommended textbooks (such as for instance slides, lecture notes, exercises, bibliography) and communications from the lecturer specific to the course can be found inside the Moodle platform › blended.uniurb.it

There are no supporting activities.

Teaching

Frontal lessons supplemented by exercises on the topics covered (4 cfu).

Attendance

Attendance at laboratory practice is compulsory in order to acquire the attendance signature and be able to take the exam.

Course books

Course books (Altenative)

L.Pavia, G.M. Lampman, G. S. Kriz “Introduction to Organic Laboratory Techniques”. Limited to the topics discussed during the lessons

Techniques in organic chemistry: Miniscale, Standard Taper Microscale, and Williamson Microscale. J. R. Mohrig, C. N. Hammond, P. F. Schatz. Limited to the topics discussed during the lessons.

Reference book

Vogel's Textbook of practical organic chemistry. Longman Scientific and Techical.

Assessment

The verification of the learning outcomes takes place through:

a) In itinere evaluations on the aptitude, results and progress obtained by the student from a technical-practical point of view in the common synthetic and extractive procedures dealt with during the practical exercises. These assessments take into account the behavior held in the laboratory and the acquisition of an autonomous practice and judgment capacity of the proposed experiences.

b) A written test, lasting 1 hour and 30 minutes, which consists in solving five exercises that follow the typology of those carried out in the classroom by the teacher. Passing the written test is necessary in order to access the oral test.

c) An oral test lasting 20-30 minutes, consisting of questions regarding both theoretical and practical aspects relating to the issues addressed during the course, and aimed at certifying the level of their knowledge and understanding reached by the student.

The written test and the oral test are aimed at ascertaining the level of knowledge and understanding achieved by the student on the theoretical/practical contents indicated in the program. Questions are asked relating both to the design of an adequate synthetic sequence and in reference to the isolation and purification techniques of the products considered. Expository skills and connection skills with other preparatory topics are also assessed.

The final grade, which takes into account the results of the written and oral tests, is expressed in thirties and reflects the overall evaluation of the candidate.

Disability and Specific Learning Disorders (SLD)

Students who have registered their disability certification or SLD certification with the Inclusion and Right to Study Office can request to use conceptual maps (for keywords) during exams.

To this end, it is necessary to send the maps, two weeks before the exam date, to the course instructor, who will verify their compliance with the university guidelines and may request modifications.

Teaching

Regular attendance of lessons favors the acquisition of the skills necessary to pass the exam. Non-attending students are invited to contact the teacher and consult the Moodle platform to acquire the teaching material.

Attendance

Attendance at laboratory practice is compulsory in order to acquire the attendance signature and be able to take the exam.

Course books

Course books (Altenative)

L.Pavia, G.M. Lampman, G. S. Kriz “Introduction to Organic Laboratory Techniques”. Limited to the topics discussed during the lessons

Techniques in organic chemistry: Miniscale, Standard Taper Microscale, and Williamson Microscale. J. R. Mohrig, C. N. Hammond, P. F. Schatz. Limited to the topics discussed during the lessons.

Reference book

Vogel's Textbook of practical organic chemistry. Longman Scientific and Techical.

Assessment

The verification of the learning outcomes takes place through:

a) In itinere evaluations on the aptitude, results and progress obtained by the student from a technical-practical point of view in the common synthetic and extractive procedures dealt with during the practical exercises. These assessments take into account the behavior held in the laboratory and the acquisition of an autonomous practice and judgment capacity of the proposed experiences.

b) A written test, lasting 1 hour and 30 minutes, which consists in solving five exercises that follow the typology of those carried out in the classroom by the teacher. Passing the written test is necessary in order to access the oral test.

c) An oral test lasting 20-30 minutes, consisting of questions regarding both theoretical and practical aspects relating to the issues addressed during the course, and aimed at certifying the level of their knowledge and understanding reached by the student.

The written test and the oral test are aimed at ascertaining the level of knowledge and understanding achieved by the student on the theoretical/practical contents indicated in the program. Questions are asked relating both to the design of an adequate synthetic sequence and in reference to the isolation and purification techniques of the products considered. Expository skills and connection skills with other preparatory topics are also assessed.

The final grade, which takes into account the results of the written and oral tests, is expressed in thirties and reflects the overall evaluation of the candidate.

Disability and Specific Learning Disorders (SLD)

Students who have registered their disability certification or SLD certification with the Inclusion and Right to Study Office can request to use conceptual maps (for keywords) during exams.

To this end, it is necessary to send the maps, two weeks before the exam date, to the course instructor, who will verify their compliance with the university guidelines and may request modifications.