ORC-30806 Structure and Reactivity

Course

Credits 6.00

Language of instruction:

English

Assumed knowledge on:

ORC-11806 Analytical Methods in Organic Chemistry; ORC-20306 Bio-organic Chemistry.

Continuation courses:

Research Methods in Organic Chemistry, MSc thesis ORC.

Contents:

Structure and Reactivity is an advanced organic chemistry course, devoted to the structure and reactivity of organic compounds, guided by organic reactions and their mechanisms. New reactions and concepts are discussed, that also allow for a more detailed understanding and use of well-known reactions. The course is targeted at Master students or BSc-3 students Molecular Life Sciences who want to deepen and broaden their knowledge of organic reactions and of the way the structure of organic molecules influences their reactivity. The following topics will be treated: radical substitution reactions, nucleophilic substitution reactions, beta-elimination reactions, electrophilic additions to carbon-carbon double bonds, electrophilic aromatic substitutions, additions of hydrides to carbonyls, reactions with phosphorus ylids, the chemistry of enols and enolates, organocatalysis, transition-metal mediated C-C bond formations, and cycloaddition reactions. Furthermore there will be short intermezzo's about stereochemical concepts (e.g. methods to prepare enantiopure compounds), the Hammett equation and recent research going on at the Lab. of Organic Chemistry.
The lectures are regularly interrupted for plenary solving and discussing questions related to the topics just discussed. These tutorials are not graded but students are strongly advised to attend all lectures and tutorials in order to be well prepared for the exam. In addition there is a short PC tutorial about computational chemistry (presence is mandatory).

Learning outcomes:

After successful completion of this course students are expected to be able to:
- analyse organic reactions as listed above and propose logical mechanisms for them;
- predict reactivity of organic compounds towards reagents, within the framework mentioned above;
- construct logical synthetic routes for given compounds;
- analyse and predict the stereochemical course of organic reactions;
- perform simple computational chemistry studies.

Activities:

- studying the theory;
- solving problems/exercises.

Examination:

The final mark is based on the result of the written examination. During the exam, all course material may be used ('open book exam'). Presence at the computational chemistry tutorial is mandatory.

Literature:

Lecture notes: Structure and Reactivity, dr. M.C.R. Franssen and prof. dr. H. Zuilhof; available at the WURshop. Course book: Organic Mechanisms: Reactions, Stereochemistry and Synthesis. Reinhard Bruckner, Michael Harmata (editor), Springer-Verlag Berlin Heidelberg, 2010, 856p. 900 illus. ISBN 978-3-642-03650-7.