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Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2006
Problem Set 3: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 7 days (10/06/06) from today (09/29/06). 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 alkoxide-induced reactions have been systematically studied by
Wharton et. al. (JOC, 1965, 30, 3254.) The illustrated substrates will undergo fragmentation to
an olefinic ketone IF the appropriate stereoelectronic constraints are met. If these constraints
cannot be met, E2 elimination to the derived bicyclic olefinic alcohol will take place.
Predict the principle product observed in each instance (B) and draw the reactive conformation
(A) that meets the stereoelectronic conditions for the reaction. Put you answers in the space
provided.
Answer:
H
OH
KOtBu
reactive conformation product
(A)
OTs
(B)
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