Study Programmes 2015-2016
CHIM0707-1  
Physical organic chemistry
Duration :
15h Th
Number of credits :
Master in chemistry (120 ECTS)2
Master in chemistry (120 ECTS)2
Master in chemistry (120 ECTS)2
Master in chemistry (120 ECTS)2
Lecturer :
Jean-Christophe Monbaliu
Language(s) of instruction :
French language
Organisation and examination :
Teaching in the second semester
Units courses prerequisite and corequisite :
Prerequisite or corequisite units are presented within each program
Course contents :
This course will benefit to students and researchers in chemistry who are interested in getting a more in-depth rationalization of reactivity in organic chemistry. CHIM0707 complements basic notions and fundamental concepts of reactivity and furnishes the appropriate tools for a deeper understanding.
This course is organized into four chapters:
Chapter I. Description of reactions
-            Thermodynamic and kinetic data
-            Fundamental mechanistic concepts
-            Structure-(re)activity relationships
Chapter II. Stereoelectronic effects
-            Fundamentals of stereoelectronic effects
-            Stereoelectronic effects and conformation
-            Stereoelectronic effects and reactivity
Chapter III. Medium effects
-            Solvents, solvation and solvent effects on reactivity
-            Ionic assistance
-            Non-conventional activation methods
Chapter IV. Stereochemistry
-            Fundamentals and terminology
-            Non-linear effects
 
Keywords: Hammett relationship; structure-(re)activity relationships; thermodynamic and kinetic control; Hammond postulate; Curtin-Hammett principle; isotopic effects; transition state theory; HSAB; nucleophilicity and electrophilicity indices; hyperconjugation; anomeric effect; anchimeric effect; substitutions on saturated carbons (SN1 and SN2); substitutions on unsaturated carbons; Baldwin rules; Hughes-Ingold rules; asymmetric induction; Felkin-Anh and Cram-chelate models; Non-linear effects in asymmetric synthesis. 
Learning outcomes of the course :
  • Get familiar with the fundamental concepts of physical organic chemistry
  • Rationalize reactivity and selectivity in organic chemistry
  • Get a finer and deeper understanding of mechanisms and their governing parameters
  • Determine and study structure-(re)activity relationships
Prerequisite knowledge and skills :
Bachelor or/and Master background in organic chemistry and physical organic chemistry is necessary.
Planned learning activities and teaching methods :
  • Lecture (80%): Delivery of theoretical background and recent examples from the literature in a lecture format. Slides are available to the students. Possibility of e-learning (online additional references and resources);
  • Group work (20%): Participatory learning, exercises.
Mode of delivery (face-to-face ; distance-learning) :
Delivery of material in a lecture format, face-to-face. Possibility of e-learning (online additional references and resources);
Recommended or required readings :
  • Modern Physical Organic Chemistry, E. V. Anslyn, D. A. Dougherty, University Science Books, 2006 (ISBN 978-1-891389-31-3)
  • Stereoelectronic effects, A. J. Kirby, Oxford University Press, 1996 (ISBN 978-0-198558-93-4)
  • Modern Solvents in Organic Synthesis, P. Knochel (Ed.), Springer, 1999 (ISBN 3-540-66213-8)
  • Recent literature (appropriate references will be delivered to illustrate the lectures)
  • Slides will be made available to the students.  Additional resources are available online (eCampus)
Assessment methods and criteria :
The theoretical and practical competences will be assessed during a written exam.
Work placement(s) :
Organizational remarks :
This course will be taught either in French or English, depending on the attendance. Slides are in English.
Contacts :
jc.monbaliu@ulg.ac.be (Jean-Christophe Monbaliu)
 
Items online :
Physical Organic Chemistry - series of lectures
Lecture 1 - Thermodynamic and Kinetic Requirements: Summary of Mechanistic Principles Lecture 2 - Linear Free Energy Relationships Lecture 3 - Stereoelectronic Effects in Organic Chemistry Lecture 4 - Solvent and Medium Effects Lecture 5 - Stereochemistry Practice