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Advanced organic chemistry

Program: 
Chemistry
ECTS: 
17
Lecturer: 
prof. dr hab. Marcin Stępień, dr hab. Ewa Dudziak, dr Alicja Kluczyk, dr hab. Piotr Stefanowicz, dr Bartosz Szyszko and other members of Organic Chemistry Department
Type: 
Compulsory
Lecture
Number of hours: 
5h X 15 weeks = 75 hours (1 semester)
Laboratory
Number of hours: 
6h X 15 weeks = 90 hours (1 semester)
Seminar
Number of hours: 
1h X 15 weeks = 15 hours (1 semester)
Objective: 

• Introduction to modern methods of organic synthesis
• acquisition of skills and knowledge related to organic synthesis and laboratory safety
• presentation of chemical and physicochemical methods of identification and determination of structure of organic compounds
• presentation of modern advanced laboratory methods used in organic synthesis
• acquiring skills necessary for safe and successful synthesis of organic compounds

Acquired Knowledge
Student
• is in possession of an extensive knowledge of organic chemistry and experimental methods used in synthetic laboratory, knows chemical concepts and theories and their influence on the development of sciences
• is in possession of an extensive knowledge of recent developments in synthetic procedures and analytical methods and safety regulations concerning organic reagents
• has knowledge of computational methods used in experimental design and data analysis
• is in possession of an extensive knowledge of the scientific equipment in organic chemistry laboratory
Acquired Skills
Student
• is able to plan the synthesis, purification and analysis of organic compounds, to perform the experiments and assess the results
• is able to search for information in professional literature, databases as well as other sources
• is able, in an advanced manner, to present research results and literature data in a written and oral form, both in Polish and English
• is able to determine the direction of further education and individual knowledge acquisition
Social competence
Student
• understand the need of continues education and constant improvement on professional competence, being able to organise the process of educating others
• is able to plan the experiments in cooperation with other students, following the safety procedures
• is able to set priorities conducive to the realization of a task appointed by himself or others right
• identifies and solves dilemmas connected with professional performance in the right way
• is able to prepare the reports according to scientific ethics, understands the need of systematic contact with scientific literature
• is aware of the responsibility bestowed on him for undertaken research, experiments or observations, understands the social aspect of practical application of the acquired expertise and responsibility which ensues

Assessment: 

lecture: written exam
seminar: midterm and final test
laboratory: written reports, assessment of laboratory work

Prerequisites: 

completed courses of analytical chemistry, inorganic chemistry and organic chemistry

Contents: 

Contemporary organic synthesis

1.  Role of organic synthesis in contemporary chemistry and chemical industry

2.  Types of synthetic transformations

3.  Oxidations and reductions in organic chemistry. Reagents and their applications

4.  Methods of carbon-carbon bond formation. Aldol-type condensations, reactions with carbanions, coupling reactions (oxidative, reductive, and catalytic)

5.  Synthesis of carbocycles

6.  Synthesis of heterocyclic and macrocyclic systems

7.  Strategy and planning in organic synthesis. Retrosynthetic analysis, synthons, umpolung

8.  Analytical methods in organic synthesis. Publication standards.

Practical organic chemistry

1.  Scientific information in the organic chemistry.

2.  Safety in the organic chemistry laboratory.

3.  How to conduct a lab book and a synthetic documentation?

4.  Modern laboratory equipment.

5.  Separation and purification of the reaction products.

6.  High vacuum techniques - vacuum/inert gas line, Schlenk techniques, vacuum distillation.

7.  Work in a controlled atmosphere.

8.  Glove-box as a convenient tool for protecting substrates/products from decomposition.

9.  Purification of reagents and solvents.

10.  Chromatography as a powerful tool for identification and separation of products.

11.  Special reaction techniques (photochemical and microwave synthesis, solid phase synthesis).

12.  Visualisation of the experimental data.

Analytical methods in organic chemistry

1.  NMR spectroscopy.

2.  Mass spectrometry.

3.  Other analytical methods useful in organic chemistry.

Laboratory

The laboratory course creates an opportunity to face all steps necessary in organic synthesis. It starts with a purification of reagents and solvents, required for further work, including a distillation in inert atmosphere. All prepared purified chemicals will be used for a microscale synthesis. Some experiments will require the use of moisture and oxygen-sensitive reagents. In this case high vacuum/inert gas Schlenk methodology will be applied. Multistep synthesis will be also conducted. The isolation and purification (crystallization, distillation and chromatography) of the final product will be an important part of the course.

Vacuum distillation will be used as a method of removal of high-boiling solvents and separation of mixtures (high vac and bulb-to bulb technique). Variety of chromatographic procedures will be also presented.