Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2010
Problem Set 1: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 14 days (11/05/10) from today (10/29/10). Grades will be administered as follows: 10
(exceptional effort), 8 (complete), 5 (incomplete or inadequate effort), 2 (poor effort), 0
(nonexistent). No late problem sets will be accepted.
1. Problem: Scheidt and co-workers discovered the following reaction catalyzed by an N-
heterocyclic carbine (J. Am. Chem. Soc. 2007, 129, 10098.) Please provide a mechanism
that accounts for the high levels of selectivity.
2. Problem: Part A: The following cycloaddition reaction was recently explored by Spino and
Perreault (Org. Lett. 2006, 8, 4385.) Provide a reasonable transition state that explains the
stereochemistry of the product.
Part B: Based on your solution above, predict the stereochemical outcome of the
cycloaddition carried out on the diastereomeric compound below. Use clear 3D drawings to
explain your answer.
3. Problem: Rodriguez and co-workers reported the following thermally induced two-
component coupling to form the fused tetracyclic product (JOC, 1999, 64, 966.) Using clear
3D drawings, provide a mechanism for the transformation that accounts for the observed