Organic Synthesis 1   (211H2)

Academic year:

2024/2025.

Attendance requirements:

201A2 + 202A2

ECTS:

7

Study level:

Study program:

Teachers:

Radomir N. Saičić, Ph.D.
full professor, Faculty of Chemistry, Studentski trg 12-16, Beograd

Filip J. Bihelović, Ph.D.
associate professor, Faculty of Chemistry, Studentski trg 12-16, Beograd

Assistants:

Filip T. Đurković
teaching assistant, Faculty of Chemistry, Studentski trg 12-16, Beograd

Andrej J. Kukuruzar
teaching assistant, Faculty of Chemistry, Studentski trg 12-16, Beograd

Hours of instruction:

Weekly: two hours of lectures + four hours of labwork (2+0+4)

Goals:

During the course the student should acquire both the theoretical knowledge in the field of organic synthesis and the manipulative skills for independent realization of the experimental procedures for the preparation of organic compounds. The course ORGANIC SYNTHESIS 1 includes functional group transformations in organic compounds. Through the lectures, students get acquainted with methods for performing oxidations, reductions, halogenations and methods for the introduction of heteroatoms into organic molecules. The course includes explanations of organic reactions, but the focus is on the preparative, practical aspect, which includes the right choice of reagents and reaction conditions in order to achieve the desired transformation with a high yield in a safe, economical and ecologically acceptable way. The main goal is to enable students to theoretically and practically perform the following types of preparative reactions: 1) oxidations, 2) reductions, 3) halogenations, 4) electrophilic aromatic substitutions by heteroatom reagents, 5) other functional transformations pertinent to organic synthesis. In addition, students should acquire routine in applying techniques of monitoring organic reactions, isolation and purification of products (chromatographic methods, distillations, crystallizations etc.), as well as in characterizing the obtained compounds.

Outcome:

The ability to independently realize basic functional group transformations in organic chemistry at the preparative level.

Teaching methods:

Lectures, experimental exercises.

Extracurricular activities:

—

Coursebooks:

Main coursebooks:

• Živorad Čeković: The Principles of Organic Synthesis (in serbian), Naučna knjiga, Belgrade, 1988.
• Zorana Ferjančić, Filip Bihelović: Preparative organic chemistry (in serbian), University of Belgrade, Faculty of Chemistry, Belgrade, 2012.
• The material available on the web page of the Department of Organic Chemistry of the Faculty of Chemistry

Supplementary coursebooks:

• Encyclopedia of Reagents for Organic Synthesis, L. Paquette Ed., J. Wiley, 1996. (available in the Library of the Faculty of Chemistry)
• Organic Syntheses, Collective Volumes 1-9 (available in the Library of the Faculty of Chemistry)

Additional material:

http://helix.chem.bg.ac.rs/~rsaicic/Organske-sinteze/

Lectures:

8 points (2 hours a week)

Syllabus:

• Introductory lecture
• Halogenation (1): Conversion of alcohols into alkyl halides and related derivatives. Addition of hydrogen halides to alkenes.
• Halogenation (2): Addition of halogens to alkenes and similar reactions. Halogenation of carbonyl compounds.
• Aromatic substitutions: halogenation, sulfonation, nitration of aromatic compounds. Nucleophilic aromatic substitutions with the formation of carbon-heteroatom bond.
• Reductions (1): Fundamentals, classification. Catalytic hydrogenations.
• Reductions (2): Reductions with metal hydrides.
• Reductions (3): Dissolving metal reductions in protic and aprotic conditions.
• Reductions (4): Other reductions:Meerwein-Ponndorf-Verley reduction, reductions with hydrazine and its derivatives, enzymatic reductions.
• Oxidations (1): Oxidations of alkanes; Oxidations of alkenes: hydroxylation and fragmentation of alkenes; Alkoxymercuration; Wacker oxidation.
• Oxidations (2): Epoxidations of alkenes (with peroxy acids; with basic hydrogen peroxide; Sharpless-Katsuki epoxidation).
• Oxidations (3): Allylic and benzylic oxidations.
• Oxidations (4): Oxidations of alcohols.
• Oxidations (5): Oxidations of glycols, phenols, carbonyl compounds, etc.
• Carbon-nitrogen and carbon-oxygen bond forming reactions.
• Synthesis of carboxylic acids derivatives and related reactions.

Labwork:

22 points (4 hours a week)

Syllabus:

Laboratory classes are of experimental nature and they include independent realization of 6 (six) preparations from the list in the Handbook and from the chemical literature.These preparations are experimental illustrations of the course units presented in the lectures and they include the practical examples of synthesizing organic compounds using the reactions of oxidation, reduction, halogenation, aromatic substitution, etc. In addition, during the realization of the preparations, students get acquainted with various techniques of isolation and purification of organic compounds, such as distillation under reduced pressure, steam distillation, continuous distillation, crystallization, etc. and are trained to routinely use these techniques in laboratory. One laboratory class deals with searching for scientific information and involves teaching students how to use scientific journals and databases.

Colloquia:

0 points

Remarks:

Students who have not passed the exam until the beginning of the course in the next school year are obliged to attend the lectures again.

Written exam:

70 points

Remarks:

Students take a written exam. In order to get a passing grade, a student has to achieve at least 50% of the points (50% of the total number of points) in the written test.