General information

Module title Organic Chemistry (Intermediate Course)
Language English
Module lecturer Donata Pluskota-Karwatka
Lecturer's email donatap@amu.edu.pl
Lecturer position profesor nadzwyczajny
Faculty Faculty of Chemistry
Semester 2021/2022 (winter)
Duration 45
ECTS 5
USOS code 02-ORGA

Timetable

Module aim (aims)

The aim of this course is to provide students with the knowledge and skills needed in modern organic synthesis with regard to retrosynthetic analysis, including planning and synthesis of chiral compounds. Students will be trained in the following.
· Reactions of selective formation of carbon-carbon and carbon-heteroatom bonds.
· Reactions and use of organometallic compounds in chemical synthesis.
· Fundamental reactions involving sulphur and phosphorus compounds;
· Retrosynthetic analysis and planning of synthesis of chiral and complex compounds;
· Safety of work in laboratory of organic chemistry ;
· Ability to use literature sources;
· Ability to communicate and work in a group.

Pre-requisites in terms of knowledge, skills and social competences (where relevant)

Advanced knowledge of organic chemistry and applied it in experiments - organic synthesis.

Syllabus

Week 1: Introduction to organic synthesis, strategies for analyzing organic reactions, electron pushing mechanisms. The synthon approach.
Week 2: Oxidation and Reduction Reactions; Distinguishing organic redox reagents and reactions from other processes; Hydrogen; Hydride reagents; Radical reductions, trapping of radicals; Transition metal oxidants: chromium, ruthenium, osmium, others Iodine, selenium and sulfur based oxidants, Peroxides, peracids, oxygen and ozone.
Week 3: Chemistry of Carbonyl Compounds; Enolates as nucleophiles (donors). Enolate equivalents with higher and lower reactivity. Carbonyl groups as electrophile (acceptors). Controlling reactivity, regioselectivity and stereoselectivity.
Week 4: Preparation and functionalization of carbon-carbon double and triple bonds. Conformational analysis of cyclohexanes Stereospecific additions and eliminations. Cyclofunctionalizations.
Week 5: Pericyclic Reactions: Cycloadditions, fragmentations and rearrangements. The effects of orbital symmetry on pericyclic reaction Diels-Alder reactions. 1,3-dipolar cycloadditions and other cycloadditions. Cope, Claisen and other sigmatropic rearrangements. Electrocyclic reactions.
Week 6: Organometallic Reagents. Lithium and magnesium reagents, preparations and reactions. Controlling reactivity, regioselectivity and stereoselectivity. Other organometallic reagents (Si, Sn, Zn, B, Cu, Pd). Transition metal catalyzed reactions - Stille, Suzuki, Negishi, Heck and other couplings. Week 7: Phosphorus in organic synthesis: Wittig reaction, Mitsunobu reaction; BINAP and Heck reaction, sulfur chemistry of garlic and onion, thioacetals, Julia olefination and Swern oxidation
Week 8: Laboratory of organic chemistry (1)
Week 9: Laboratory of organic chemistry (2)
Week 10: Laboratory of organic chemistry (3)
Week 11: Laboratory of organic chemistry (4)
Week 12: Laboratory of organic chemistry (5)
Week 13: Laboratory of organic chemistry (6)
Week 14: -
Week 15: Exam

Reading list

J. Clayden, N. Greeves, S. Warren, P. Wothers: Organic Chemistry. Oxford University Press, 2005. · F. A. Carey, R. J. Sundberg Advanced Organic Chemistry Part B – Reactions and Synthesis. 4th ed., Kluwer Academic Publishers, 2002 · J. March: Advanced Organic Chemistry, Reactions, Mechanisms and Structure. 6th ed. Wiley-VCH New York, 2007. ·I. Ojima, Catalytic Asymmetric Synthesis. Wiley-VCH New York 2010. ·T. Laue, A. Plagens, Named Organic Reactions. Wiley, 2002. · K.C. Nicolaou, E.J. Sorensen Classics in Total Synthesis. Targets, Strategies, Methods. 4th rep. Wiley –VCH, New York, 2003. · S.D. Burke, R.H. Danheiser, oxidizing and reducing agents. Handbook of reagents for organic synthesis. Wiley, New York, 2000. · A.J. Pearson, W.R. Roush, Activating agents and protective groups. Handbook of reagents for organic synthesis. Wiley, New York, 2001. · The articles in the scientific journals recommended by lecturer and teaching staff.