Organic Synthesis 2   (1212H)

Academic year:

2012/2013.

Attendance requirements:

1211H

ECTS:

9

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 + seven hours of labwork (2+0+7)

Goals:

During the course students should should be enabled, both at the theoretical and practical level, to realize independently syntheses of simple organic compounds. Organic Synthesis 2 includes the review 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 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 a high yield, in a safe, economical and ecologically acceptable way. In addition, students are trained in using of chemical literature and data-bases (in electronic and paper forms) in order to find a full scientific information about a chemical compound, reaction or a process.

Outcome:

Capacity to perform independently syntheses of small organic molecules.

Teaching methods:

Lectures, labworks.

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:

• 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 of organotransition metal complexes.
• Preparation and reactions of organometallic compounds (4): Synthetic applications of organotransition metal 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 carbanions. Umpollung.
• Alkylation (4): Michael addition, Robinson annulation. Reactions of cyanide and acetylide anions.
• Acylation.
• Aldol reaction (1): Base catalyzed aldol reaction under protic conditions.
• Aldol reaction (2): Acid-catalyzed aldol reactions under protic conditions.
• Aldol reaction (3): Directed aldol 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 cubstitutions with formation of carbon-carbon bond.
• Aromatic substitutions (2): Nucleophilic aromatic substitutions with formation of carbon-carbon bond.

Labwork:

22 points (7 hours a week)

Syllabus:

Labworks includ independent realization of 7 (seven) preparations from the list in the Handbook, as well as from the chemical literature. Some preparations include several steps, the product of the former reaction being the substrate in the latter. The last preparation is not done experimentally, but is prepared theoretically, from the literature. These preparations are the experimental illustrations of the topics given in the lectures and encompass the concrete examples of synthesis of organic compounds by applying various reactions for the formation of the carbon-carbon bond. In addition, students become familiar with various techniques for the isolation and purification of organic compounds. In addition to techniques learned during the course Organic Synthesis 1, the techniques of "flash chromatography", "dry-flash chromatography", liquid chromatography and sublimation will be introduced. One term involves the search for a scientific information and the examination of student's capacity 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 (i. e. min. 50% of the maximum score).