C4450 Organic Chemistry III -synthesis

Faculty of Science
Spring 2009
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. RNDr. Ctibor Mazal, CSc. (lecturer)
doc. Mgr. Kamil Paruch, Ph.D. (lecturer)
Guaranteed by
doc. Mgr. Kamil Paruch, Ph.D.
Department of Chemistry – Chemistry Section – Faculty of Science
Timetable
Mon 14:00–15:50 A08/309
Prerequisites
C3022 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
there are 18 fields of study the course is directly associated with, display
Course objectives
Content of the subject is a logical extension of introductory classes Organic Chemistry I (C2021) and Organic Chemistry II (C3050). The major goal is to provide a comprehensive overview of modern synthetic methods routinely used in laboratories and even in industry.
Syllabus
  • 1.General terms and principles. Summary of the important facts from other subjects.Hammond, Curtin-Hammett principle, principle of mikroscopic reversibility, Baldwin's rules, kinetic and thermodynamic course of reactions, factors influencing selectivity of the reactions. Application of these terms in organic synthesis.
  • 2.Enolate chemistry. Enolate preparation and selectivity of their formation. Various methods of the enolate preparation. 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. Classical reactions(Corey, Woodward, Nicolaue). Synthetic project.
  • 13.Protection groups and their application.
  • 14.Modern organic synthesis. Combinatorial chemistry.
Literature
  • CAREY, Francis A. and Richard J. SUNDBERG. Advanced Organic Chemistry, Part B. New York: Plenum Press, 1990, 800 pp. info
  • SMITH, Michael. Organic synthesis. New York: McGraw-Hill, 1994, xxx, 1595. ISBN 0070487162. info
  • FUHRHOP, Jurgen and Gustav PENZLIN. Organic Synthesis. New York: VCH, 1994, 432 pp. info
  • LIŠKA, František. Organická syntéza : syntonový přístup. 1. vyd. Praha: Vysoká škola chemicko-technologická, 1993, 339 s. ISBN 80-7080-176-X. info
Assessment methods
Lecture with written test followed with an oral examination.
Language of instruction
Czech
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 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 2022, Spring 2023, Spring 2024, Spring 2025.
  • Enrolment Statistics (Spring 2009, recent)
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