Chemistry 560: Organic Synthesis: A Mechanistic Approach

Course Level: 
Graduate Level
Academic Year: 


Jolene Reid ( )

Office Hours:      TBD

Prerequisites:     Chem 203; Chem 213; Chem 330



There are no required textbooks for this course.  Throughout the course, we will assign readings from handouts, portions of book chapters (uploaded on Connect) and the primary literature.

Reference Texts:  (available in the main library unless otherwise indicated)

Recommended for your personal collection:

Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. Organic Chemistry (2001)
Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry
Carey, F. A., Sundberg, R. J. Advanced Organic Chemistry, Part A and B (2000)

Problem Sets:

There will be periodic problem sets, which will be worth 15% of your grade.

Problem sets will both complement material covered in lecture and introduce new concepts not covered during class.  Answers to these problem sets will be posted on the course website.  Students may be examined on material contained within the problem sets. 

Comments on the 460/560 split:

Chemistry 560 students have additional course requirements beyond Chem 460.

In addition to the standard course material, Chemistry 563 students may have (a) additional examination questions, (b) different examination formats, (c) additional required reading, and (d) additional problem sets.


There will be two midterms and a final.  If all problem sets are turned in with a passing average, then a passing grade on the final guarantees a passing grade in the course.

Course Contents (Tentative)

1.   Bonding Theories

2.   Predicting Reactivity Outcomes

3.   Review of Arrow Pushing Mechanisms/Mechanistic Similarities

4.   Organic Chemistry Using Phosphorous-Based Reagents

5.   Organic Chemistry Using Sulfur-Based Reagents

6.   Metal-Mediated Reactivity

7.   Acyclic Conformation

8.   Cyclic Conformation

9.   Reactivity of Ring Systems

10.  Ring Forming Reactions

11.  Pericyclic Reactions 1

12.  Pericyclic Reactions 2

13.  Pericyclic Reactions 3

14.  Cyclic Transition States:  Boron-Based Reagents

15.  Atom Migration Reactions

16.  Radical Reactivity

17.  Building Chiral Molecules 1

18.  Building Chiral Molecules 2

19.  Analyzing Reaction Mechanisms

20.  Thermodynamics

21.  Chemistry of carbenes

22.  Special Topics 1

22.  Special Topics 2

23.  Special Topics 3