Learning outcomes

Students who complete this course will:
 
- understand FMO theory and its application to reactivity and stereoelectronic effects
- be able to manipulate and rationalise advanced synthetic methods based on main group elements
- have a detailed knowledge of the properties of aromatic compounds and of the concept of aromaticity
- have an advanced level of knowledge in heteroaromatic, alicylic and in the principles of asymmetric synthesis
- have acquired an advanced understanding of the physical organic chemistry of pericyclic reactions, including the Woodward-Hoffmann rule, and will be able to use these principles to understand or predict (regio/stereo)selectivity in these reactions
 
 

 

Goals

The Advanced Organic Chemistry lectures aim to familiarise students with the main aspects of contemporary organic synthesis :

- physical organic chemistry, especially pertaining to the electronic structure of molecules;

- advanced synthetic methods, including radical and heterocyclic chemistry, pericyclic reations and asymmetric synthesis and catalysis.

 

Content

The course is subdivided into two parts.

Part A: Organic chemistry and reactivity

This part tackles 4 main aspects: the chemistry of main group elements (part 1), heteroaromatic compounds and their properties (part 2), aromatic compounds and aromaticity (part 3), and the reactivity of organic molecules (part 4).

Part B: Advanced Organic Synthesis:

this part deals with advanced topics in ring formation and editing of ring size, hetereoatomatic synthesis, asymmetric synthesis and catalysis, pericylic reactions and the use of heteroatoms in synthesis.

 

Table of contents

Part A: Advanced Reactivity of Organic Molecules


I. Organo-main group chemistry
II. Properties, structures and reactivities of heteroaromatic compounds
III. Aromatic Compounds and Aromaticity
IV. Chemical Reactivity in organic chemistry

Part B: Advanced Synthetic Methods

I. Saturated carbocycles
II. Saturated heterocycles
III. Radical Reactions
IV. Polar Rearrangements, ring expansions and contractions
 
V. Pericyclic Reactions

VI. Asymmetric Synthesis and Catalysis

 

Exercices

Exercises are avaible online.

Assessment method

The course is evaluated in a three-hour written examination based on the lectures and exercises.

A mark of 5/20 or less in one part of the exam automatically entails a failure in the whole exam.

Marks greater than 10/20 on one part of the exam are not conserved for further exam session or in subsequent years.

Sources, references and any support material

The lecture slides are available in PDF format.

J. Clayden, N. Greeves, S. Warren, P. D. Wothers « Organic Chemistry », 2nd Edition, Oxford University Press

S. Warren, P. Wyatt « Organic Synthesis: The Disconnection Approach», Second Edition, Wiley; S. Warren, P. Wyatt « Organic Synthesis: Strategy and Control», Wiley; R. Brückner « Advanced Organic Chemistry: Reaction Mechanisms », Academic Press; K. C. Nicolaou, E. J. Sorensen « Classics in Total Synthesis », Wiley-VCH; K. C. Nicolaou, S. A. Snyder « Classics in Total Synthesis II », Wiley-VCH; L. Kürti, B. Czakó « Strategic Applications of Named Reactions in Organic Synthesis », Elsevier.

Ansylyn & Dougherty, Modern Physical Organic Chemistry; N. T. Anh, Frontier Orbitals, a practical manual; A. Carey, F. A. and Sundberg,; R. J. Advanced Organic Chemistry; Parts A (Fourth Edition) and B. (Fourth Edition); B. Kirby, A. J. Stereoelectronic Effects; March, J. Advanced Organic Chemistry. Fourth Edition; Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry.

 

 

Language of instruction

Anglais