C4450 Organic Chemistry III - synthesis

Faculty of Science
Spring 2022
Extent and Intensity
2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
Teacher(s)
doc. Mgr. Kamil Paruch, Ph.D. (lecturer)
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
Thu 9:00–10:50 A08/309
Prerequisites
( C3022 Organic Chemistry II/1 || C3050 Organic Chemistry II )&& C5500 Stereochemistry of Org. Comp. && C7410 Structure and Reactivity
General, organic and physical chemistry
Course Enrolment Limitations
The course is also offered to the students of the fields other than those the course is directly associated with.
fields of study / plans the course is directly associated with
Course objectives
The course is a logical extension of introductory classes Organic Chemistry I (C2021) and Organic Chemistry II (C3050). The major goal is to provide the students with a comprehensive overview of modern synthetic methods routinely used in the organic chemistry laboratory and in industry, so that the students will be able to apply them in planning of effective preparations of organic compounds.
Learning outcomes
After passing the course, students will be able to design viable syntheses of organic molecules using traditional and modern methods of organic synthesis.
Syllabus
  • 1.General terms and principles and their application in organic synthesis.
  • 2.Enolate chemistry. Preparation of enolates and selectivity of their formation. Usage of enolates in organic synthesis. Stereoselective reactions of enolates.
  • 3.Enolate chemistry. Aldol reaction, Claisen reaction. Stereoselective reaction. Double stereodifferentiation. Wittig and Petersen reaction. Chemistry of sulfur ylides. Corey-Tchaykovsky reaction.
  • 4.Selective nucleophilic additions to carbonyl group. Cram, Karabatsos, Felkin-Ahn and Heathcock models.
  • 5.Interconversions of functional groups.
  • 6.Interconversions of functional groups. Mitsunobu, Eschenmoser reactions, hydroborations. Iodolactonization.
  • 7.Oxidation. Swern, Dess-Martin, Oppenauer, Sharpless and Jacobsen oxidation. Synthetic application. Epoxidation, dihydroxylation, preparation of vicinal aminoalcohols.
  • 8.Reduction. Shapiro, Birch reduction. Catalytic hydrogenation, diimide reactions, hydrosilylations.
  • 9.Rearrangements, pericyclic reactions. Cope, Claisen rearrangement. Diels-Alder, ene reactions and their hetero modifications.
  • 10.Organometallic reactions. Grignard reagents, Stille, Suzuki and McMurry reactions, conjugate addition of organocuprates, reactions of organozinc reagents. Palladium reactions.
  • 11.Multicomponent reactions. Mannich, Strecker, Ugi reactions and their stereoselective examples.
  • 12.Multistep synthesis.
  • 13.Protection groups and their application.
  • 14.Modern organic synthesis. Combinatorial chemistry.
Literature
    recommended literature
  • KÜRTI, László. Strategic applications of named reactions in organic synthesis : background and detailed mechanisms. Edited by Barbara Czakó. Amsterdam: Elsevier, 2005, lii, 758. ISBN 0124297854. info
  • BEŇOVSKÝ, Petr. Organická chemie : organická syntéza. 1. vyd. Brno: Masarykova univerzita, 2003, vi, 280. ISBN 8021032812. info
    not specified
  • Science of synthesis. Edited by Keiji Maruoka. Stuttgart: Georg Thieme, 2012, xliii, 974. ISBN 9783131693716. info
  • Encyclopedia of reagents for organic synthesis. Edited by Leo A. Paquette. 2nd ed. Chichester: Wiley, 2009, ccxx, 627. ISBN 9780470017548. info
  • Organic reactions. Edited by S.E Denmark. New York: John Wiley & Sons, 2009. ISBN 9780470423745. info
Teaching methods
theory plus design of viable organic syntheses
Assessment methods
In the course of the semester, students will pass 2-3 tests covering the corresponding topics. The final exam consists of a written and an oral part. Evaluation is focused on students' ability to design viable organic synthesis plus understanding of scope and limitations of used organic transformations.
Language of instruction
English
Further Comments
Study Materials
The course is taught annually.
Listed among pre-requisites of other courses
The course is also listed under the following terms Spring 2008 - for the purpose of the accreditation, Spring 2011 - only for the accreditation, Spring 2000, Spring 2001, Spring 2002, Spring 2003, Spring 2004, Spring 2005, Spring 2006, Spring 2007, Spring 2008, Spring 2009, Spring 2010, Spring 2011, Spring 2012, spring 2012 - acreditation, Spring 2013, Spring 2014, Spring 2015, Spring 2016, Spring 2017, spring 2018, Spring 2019, Spring 2020, Spring 2021, Spring 2023, Spring 2024, Spring 2025.
  • Enrolment Statistics (Spring 2022, recent)
  • Permalink: https://is.muni.cz/course/sci/spring2022/C4450