Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2005
Problem Set 4: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 7 days (10/14/05) from today (10/07/05). 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: Provide a mechanism for the following which is consistant with the principles of
orbital symmetry. Assign the expected relative stereochemistry in the product (TL, 1986, 295).
Me Me O
2. Problem: The carbonyl ene reaction is illustrated below. Using FMO analysis, evaluate the
transition state of this reaction. Your answer should include: a transition state drawing; clear
orbital depictions and HOMO-LUMO assignments; an indication of the number of
electrons from each segment; and an indication of whether the reaction is thermally