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Advanced organic chemistry

Program: 
Chemistry
ECTS: 
17
Lecturer: 
dr hab. Marcin Stępien, 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)
Assessment: 

Ways of earning credits for the completion of a course /particular component, methods of assessing academic progress:
1. lecture: written exam
2. seminar: evaluation based on presentations, test
3. laboratory: evaluation based on discussions, work assessment and written reports

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.