C6180 Advanced laboratory course in organic chemistry

Faculty of Science
Autumn 2018
Extent and Intensity
0/0/5. 5 credit(s) (plus extra credits for completion). Type of Completion: z (credit).
Teacher(s)
Benoit Jean-Pierre Carbain, PhD. (seminar tutor)
doc. Mgr. Kamil Paruch, Ph.D. (seminar tutor)
Guaranteed by
doc. Mgr. Kamil Paruch, Ph.D.
Department of Chemistry - Chemistry Section - Faculty of Science
Supplier department: Department of Chemistry - Chemistry Section - Faculty of Science
Timetable
Mon 17. 9. to Fri 14. 12. Mon 16:00–17:50 A10-316, Tue 9:00–11:50 A10-316
Prerequisites
Organic chemistry II (C2021) Organic chemistry III - synthesis (C4450)
Course Enrolment Limitations
The course is only offered to the students of the study fields the course is directly associated with.
Fields of study the course is directly associated with
Course objectives
The goal of the practical course C6180 is to get students to become familiar with traditional and modern methods of organic synthesis. Each student will carry out assigned multistep synthesis, whose part will be a brief review of key reactions (e.g. Diels-Alder reaction, Suzuki coupling, ozonolysis, Friedel-Crafts acylations etc.) used in the individual synthetic steps. Students will purify the intermediates and target compounds; they will also get familiar with the most frequently used techniques of structural analysis of organic compounds, namely those based on NMR. At the end of the course, students will be able to independently carry out a multistep synthesis, purification as well as structural characterization of organic compounds of medium complexity.
Learning outcomes
After passing the course, students will be capable of carrying out several-steps organic synthesis in the laboratory as well as interpreting the NMR spektra of organic compounds of medium complexity.
Syllabus
  • Helicenebisquinones: reduction of quinones, alkylation of phenols, phase transfer catalysis, Friedel-Crafts acylation, preparation of silylenolethers, Diels-Alder reaction, oxidation of hydroquinones to quinones. Pyrazolo[1,5-a]pyrimidines: cyclizations, regioselective halogenations of heterocyclic compounds, nucleophilic substitutions, introduction and removal of protecting groups, palladium catalyzed reactions, separation of enantiomers using HPLC on chiral stationary phase. Substituted cyclopentanes: regioselective addition to electron-defficient alkynes, preparation of cyclopentadiene, Diels-Alder reaction, dihydroxylation, ozonolysis, reduction with hydrides, use of silylethers-based protecting groups. Supramolecular building blocks based on glycoluril and [1.1.1]bicyclopentane: nucleophilic substitution of benzylhalides, Staudinger reduction, cyclodimerization, handling of methyllithium and butyllithium.
Literature
    required literature
  • Organic syntheses. Edited by Jeremiah P. Freeman. Rev. ed. New York: John Wiley & Sons, 1993. 696 s. ISBN 0471585653. info
    recommended literature
  • Encyclopedia of reagents for organic synthesis. Edited by Leo A. Paquette. Chichester: Wiley, 2009. s. i-xviii. ISBN 9780470017548. info
  • Organic reactions. Edited by S.E Denmark. New York: John Wiley & Sons, 2009. ISBN 9780470423745. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 1, Additions to c-x [pí] bonds. Part 1. Edited by Barry M. Trost - Ian Fleming - Stuart L. Schreiber. 1st ed. Oxford: Pergamon Press, 1991. xxi, 989 s. ISBN 0-08-040592-41. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 2, Additions to c-x [pí] bonds. Part 2. Edited by Barry M. Trost - Ian Fleming - Clayton H. Heathcock. 1st ed. Oxford: Pergamon Press, 1991. xxiii, 123. ISBN 0-08-040593-42. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 3, Carbon-carbon [sigma]-bond-formation. Edited by Barry M. Trost - Ian Fleming - Gerald Pattenden. 1st ed. Oxford: Pergamon Press, 1991. xxi, 1186. ISBN 0-08-040594-43. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 4, Additions to and substitutions at c-c [pí] bonds. Edited by Barry M. Trost - Ian Fleming - Martin F. Semelhack. 1st ed. Oxford: Pergamon Press, 1991. xxi, 1299. ISBN 0-08-040595-44. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 5, Combining c-c [pí] bonds. Edited by Barry M. Trost - Ian Fleming - Leo A. Paquette. 1st ed. Oxford: Pergamon Press, 1991. xxv, 1333. ISBN 0-08-040596-75. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 6, Heteroatom manipulation. Edited by Barry M. Trost - Ian Fleming - Ekkehard Winterfeldt. 1st ed. Oxford: Pergamon Press, 1991. xxi, 1194. ISBN 0-08-040597-56. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 7, Oxidation. Edited by Barry M. Trost - Ian Fleming - Steven V. Ley. 1st ed. Oxford: Pergamon Press, 1991. xxv, 1012. ISBN 0-08-040598-37. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 8, Reduction. Edited by Barry M. Trost - Ian Fleming. 1st ed. Oxford: Pergamon Press, 1991. xxv, 1139. ISBN 0-08-040599-18. info
  • Comprehensive organic synthesis : selectivity, strategy & efficiency in modern organic chemistry. Volume 9, Cumulative indexes. Edited by Barry M. Trost - Ian Fleming. 1st ed. Oxford: Pergamon Press, 1991. xv, 810 s. ISBN 0-08-040600-99. info
Teaching methods
theoretical preparation, laboratory course, individual discussions with the lecturer
Assessment methods
Evaluation consists of two parts: 1. overall yield and purity of the final product and individual iontermediates. 2. ability of the student to suggest alternative routes for the synthetic steps.
Language of instruction
Czech
Further Comments
Study Materials
The course is taught annually.
The course is also listed under the following terms Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2019.
  • Enrolment Statistics (Autumn 2018, recent)
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