Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2006
Problem Set 10: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 10 days (12/11/06) from today (12/01/06). Grades will be administered as follows: 5
(exceptional effort), 4 (complete), 3 (incomplete or inadequate effort), 2 (poor effort), 0
(nonexistent). No late problem sets will be accepted.
1. Problem: The following sets of transformations provide us with some very interesting chemical
transformations. Please provide the mechanisms for each transformation and discuss the
stereochemical outcome of the 5-membered carbacycle.
2. Problem: Please provide the mechanism for the following reaction with Cu(acac)2. Rationalize
the cis:trans ratio using what we've learned in the course so far. (Hint: The mechanism should
include a homolytic based pathway).
3. Problem: Please provide the mechanism for the following transformation illustrated below.
Account for the equivalents of reagents being used. Although stereochemistry is not indicated,
provide the predicted stereochemical outcome for the following transformation.