Organic Synthesis 1   (1211H)

Academic year:

2012/2013.

Attendance requirements:

1201A + 1202A

ECTS:

7

Study level:

Study program:

Teacher:

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

Assistants:

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

Bojan Z. Vulović, Ph.D.
assistant professor, Faculty of Chemistry, Studentski trg 12-16, Beograd

Miloš D. Trajković, Ph.D.

Jasna J. Marjanović Trajković, Ph.D.

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 groups transformations in organic compounds. Through the lectures, students get acquainted with methods for performing oxidations, reductions, halogenations and methods of introduction of heteroatoms in organic molecules. The course includes mechanistic explanations of organic reactions, but the point is on a preparative, practical aspect, which includes the right choice of reagents and reaction conditions, in order to effect the desired transformation in high yield, in a safe, economical and ecologically acceptable way. Goals: to enable student theoretically and practically to execute independently 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, 6) acquiring routine in applying techniques of monitoring organic reactions, isolation and purification of products (chromatography methods, distillations, crystallizations etc.), as well as in characterizing the obtained compounds, 7) Using chemical literature and data-bases (in paper and electronic forms) in order to find complete information about the chemical compound, reaction or a process.

Outcome:

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

Teaching methods:

Lectures, labwork.

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.
• Lecture notes available at the web site of the Chair of Organic Chemistry, Faculty of Chemistry

Supplementary coursebooks:

• Encyclopedia of Reagents for Organic Synthesis, L. Paquette Ed., J. Wiley, 1996.
• Organic Syntheses, Collective Volumes 1-9.
• Vogel's Textbook of Practical Organic Chemistry, 4th edition, Longman, London, 1981.

Additional material:

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

Lectures:

8 points (2 hours a week)

Syllabus:

• Introductory lecture.
• Halogenations (1): Conversion of alcohols into alkyl halides and related derivatives. Addition of hydrogen halides to alkenes.
• Halogenations (2): Additions of halogens to alkenes and related reactions. Halogenations of carbonyl compounds.
• Halogenations (3): Methods of preparing organofluorine compounds.
• Aromatic substitutions: halogenation, sulfonation, nitration of aromatic compounds. Nucleophilic aromatic substitutions with formation of carbon-heteroatom bond.
• Reductions (1): Fundamentals, classification. Catalytic hydrogenations.
• Reductions (2): Reductions with metal hydrides.
• Reductions (3) Dissolving metal reductions.
• Reductions (4): Other reductions: Meerwin-Pondorf-Verley reduction, reductions with hydrazine and 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.
• Oxidation (5): Oxidations of glicols, phenols, carbonyl compounds etc.
• Closing lecture

Labwork:

22 points (4 hours a week)

Syllabus:

Labwork include independent realization of 6 (six) preparations from the list in the Handbook, as well as from the chemical literature. These preparations are the experimental illustrations of the material exposed in lectures and involve the concrete examples of synthesis of organic compounds using the reactions of oxidation, reduction, halogenation, aromatic substitution etc. In addition, during the course of preparation, 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 they are trained in a routine use of these techniques in laboratory work. One term of labwork deals with search for a scientific information and involves teaching students how to use journals and data-bases.

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. They do not have to do the lab works again, but they have to pass the written examination in order to qualify for the final exam.

Written exam:

70 points

Remarks:

Written exam. To pass the exam, the threshold at the written examination is 50% of correct answers (50% of the maximum score).