Organic Synthesis II - MC270P13B
Title: Organic Synthesis II
Czech title: Organická syntéza II
Guaranteed by: Department of Organic Chemistry (31-270)
Faculty: Faculty of Science
Actual: from 2024
Semester: summer
E-Credits: 4
Examination process: summer s.:combined
Hours per week, examination: summer s.:2/2, C+Ex [HT]
Capacity: unlimited
Min. number of students: 3
4EU+: no
Virtual mobility / capacity: no
State of the course: taught
Language: English
Note: enabled for web enrollment
priority enrollment if the course is part of the study plan
Guarantor: doc. Mgr. Radim Hrdina, Ph.D.
Opinion survey results   Examination dates   
Annotation -
Organoelement chemistry in organic synthesis, chemistry of organolithium compounds, chemistry of organomagnesium compounds, chemistry of organocopper compounds, chemistry of organozinc compounds, chemistry of organoboron compounds, chemistry of organosilicon compounds, chemistry of organotin compounds, chemistry of organophosphorus compounds, chemistry of organosulphur compounds, chemistry of hypervalent iodine compounds, protecting groups in organic synthesis.

This course is for ERASMUS students also available in English.
Last update: Hrdina Radim, doc. Mgr., Ph.D. (04.09.2024)
Literature -

Recommended literature:
1. Francis A. Carey, Richard J. Sundberg: Advanced Organic Chemistry, Part B - Reaction and Synthesis, Springer, 2007, ISBN: 038768350X.
2. J. Svoboda: Organická syntéza, VŠCHT Praha, 2017, ISBN: 978-80-7080-990-7.
3. P. Warren, P. Waytt: Organic Synthesis: The Disconnection Approach, Wiley, Chichester, United Kingdom, 2008.

Other books:

Laszlo Kurti, Barbara Czako: Strategic Applications of Named Reactions in Organic Synthesis, Academic Press, 2005, ISBN: 9780124297852.
Michael Smith: Organic Synthesis. Academic Press, 2011, ISBN: 9781890661403.
L. Lešetický, M. Dzurrila, P. Elečko, M. Potáček, P. Zahradník: Organická syntéza, SPN Praha, 1983.
V. Dědek, L. Lešetický, F. Liška, J. Svoboda: Organická syntéza. Transformace funkčních skupin. Karolinum, Praha 1995.

Last update: Hrdina Radim, doc. Mgr., Ph.D. (04.09.2024)
Requirements to the exam -

Requirements for study control:

credit - oral presentation about the selected synthetic organic method
exam - first part (written part with a score above 60%), the second part (oral)

 

Last update: Hrdina Radim, doc. Mgr., Ph.D. (04.09.2024)
Syllabus -

Syllabus Organic Synthesis II

1. Structure, preparation and reactivity of organolithium compounds

2. Structure, preparation and reactivity of organomagnesium compounds

3. Structure, preparation and reactivity of organocopper compounds

4. Structure, preparation and reactivity of organozinc compounds

5. Structure, preparation and reactivity of organoboron compounds

6. Structure, preparation and reactivity of organosilicon compounds

7. Structure, preparation and reactivity of organotin compounds

8. Structure, preparation and reactivity of organophosphorus compounds

9. Structure, preparation and reactivity of organosulfur compounds

10. Structure, preparation and reactivity of hypervalent iodine compounds

11. Protective groups in organic synthesis (protection and deprotection of functional groups (-OH, -NH2, -COOH, COR))

Last update: Hrdina Radim, doc. Mgr., Ph.D. (04.09.2024)
Learning outcomes -

Upon completion of the course, students will be able to design the preparation of organometallic or organoelement starting materials and apply them to the preparation of complex organic compounds. The student will use organometallic compounds based on Li, Mg, Cu, Zn, Sn and boron compounds especially for C-C bond formation reactions and addition reactions on polarized multiple bonds. Boron and silicon compounds will be used in the reduction of organic compounds with multiple bonds. Student will use compounds based on hypervalent iodine mainly for oxidation reactions of organic compounds. The phosphorus compounds will be used in a number of the following organic transformations: the Wittig reaction, the Mitsunobu reaction, the Appel reaction, the Corey-Fuchs reaction, the Morita-Bayliss-Hillmann reaction, the Cadogan reaction, the Studinger reaction, the Lawesson reaction, the Kukhtin-Ramirez reaction, and as ligands in reactions catalysed by transition metal complexes such as hydrogenation reactions of multiple CC bonds. Sulfur compounds are mainly used for the following transformations: for dehydration reactions, for oxidation reactions of alcohols to aldehydes, hence ketones, for epoxidation reactions, for the formation of C=C double bonds by elimination reactions and condensation (in the sense of formation of a C=C bond between two reactants) reactions, for the formation of alkyl radicals and their subsequent transformations.  In planning the synthesis of a complex organic substance, the student will be able to evaluate which protecting groups are appropriate for a particular sequence of reactions depending on the environment (acidic, basic, reducing, oxidising) in which the reactions proceed.

Last update: Hrdina Radim, doc. Mgr., Ph.D. (05.09.2024)