Organic Synthesis 2   (212H2)

Academic year:

2024/2025.

Attendance requirements:

211H2

ECTS:

9

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

Ivan S. Borković
junior teaching assistant, Faculty of Chemistry, Studentski trg 12-16, Beograd

Hours of instruction:

Weekly: two hours of lectures + seven hours of labwork (2+0+7)

Goals:

This course should enable students to independently realize the syntheses of simple organic compounds at both theoretical and practical level. Organic Synthesis 2 includes an overview of the most important reactions for the carbon-carbon bond formation, including reactions of organometallic compounds, alkylations, acylations, aldol reaction, reactions of phosphorus and sulfur ylides, aromatic substitutions and cycloadditions and their application in organic synthesis. The course includes mechanistic 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. In addition, students are trained to use chemical literature and databases (in electronic and paper forms) in order to find relevant scientific information about a chemical compound, reaction or a process.

Outcome:

Students will be able to independently perform the synthesis of small organic molecules.

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.
• 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. (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:

• Preparation and reactions of organometallic compounds (1): Grignard reagent.
• Preparation and reactions of organometallic compounds (2): Organolithium compounds, organozinc compounds.
• Preparation and reactions of organometallic compounds (3): Basic reactions of organotransition metal complexes.
• Preparation and reactions of organometallic compounds (4): Synthetic applications of organometallic complexes of transition metals complexes: cross couplings (Stille, Suzuki and Negishi coupling), the Heck reaction, alkene metathesis.
• Alkylation (1): Generation and reactivity of enolate anions. Alkylation of ketones.
• Alkylation (2): Alkylation of enamines. Methylene active compounds: alkylation and transformations of malonic, acetoacetic ester and 1,3-dicarbonyl compounds.
• Alkylation (3): Alkylation of esters and carboxylic acids dianions. Alkylation of sulfur-stabilized anions. Umpolung.
• Alkylation (4): Michael addition, Robinson annulation. Reactions of cyanide and acetylide anions.
  Acylation.
• Aldol reaction (1): Base-catalyzed aldol reactions under protic conditions.
• Aldol reaction (2): Acid-catalyzed aldol reactions under protic conditions. Intramolecular aldol reaction.
• Aldol reaction (3): Directed aldol reactions (reactions under aprotic conditions); The Mannich reaction.
• Ylides: Preparation and reactions of phosphorus and sulfur ylides.
• Cycloadditions (1): The Diels-Alder reaction.
• Cycloadditions (2): 2+2 cycloadditions.
• Aromatic substitutions (1): Electrophilic aromatic substitutions with the formation of carbon-carbon bond.
• Aromatic substitutions (2): Nucleophilic aromatic substitutions with the formation of carbon-carbon bond.

Labwork:

22 points (7 hours a week)

Syllabus:

Laboratory classes are of experimental nature and they include independent realization of 7 (seven) preparations from the list in the Handbook and from the chemical literature.Some preparations include several steps since the product of one reaction is used as the substrate in the next. These preparations represent experimental illustrations of the course units covered in the lectures and include clear examples of the synthesis of organic compounds by applying various reactions for the formation of the carbon-carbon bond. Apart from that, within some preparations, students will become familiar with various techniques used for the isolation and purification of organic compounds. In addition to the techniques introduced within the course Organic Synthesis 1, the techniques of "flash chromatography", "dry-flash chromatography", liquid chromatography, sublimation, etc. will be introduced.

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:

The students take a written exam. In order to get a passing grade, one has to correctly solve at least 50% of the problems (i.e. achieve 50% of the total number of points) on the written test.