Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2007
Problem Set 2: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 7 days (09/21/07) from today (09/14/07). 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: Predict the most stable conformation of the indicated dioxospiran. Use MO's to
tailor your answer.
Please see: http://chem.wayne.edu/andreanagroup/ for answers to this question
2. Problem: The formation of ketals (acetals) from ketones is usually a straightforward
operation. However, it was found that treatment of unsaturated ketone 1 with pTsOH and
ethylene glycol did not provide the expected ketal, but the aromatic compound 2 as the major
product (Tetrahedron 1965, 21, 2297). Provide a plausible mechanism for this reaction.