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Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2006
Problem Set 4: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 7 days (10/13/06) from today (10/06/06). 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 Lewis acid mediated cyclization occurs in two steps as noted below.
With your current understanding of mechanisms, please provide in great detail all of the steps
that occur in this transformation while including a rational for stereochemical outcomes.
CO2Me
O O
CO2Me
1) BF3
.
OEt2, CH2Cl2
-78 o
C to 10 o
C
3 hr, 93%
2) BF3
.
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