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CHM 7200 Organic Structures and Mechanisms Fall Term 2005 Problem Set 2: This problem set is now available at (www.blackboard.wayne.edu). It will be due in
 

Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2005
Problem Set 2: This problem set is now available at (www.blackboard.wayne.edu). It will be due in
class 7 days (09/23/05) from today (09/16/05). 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: Predict the most stable conformation of the indicated dioxospiran. Use MO's to tailor your
answer.
O
O
Answer:
The most stable conformation of the 1,7-dioxaspiro[5.5]undecane can be predicted by considering the
anomeric effect imposed on this spiro ring system. Fully saturated, six-membered ring systems assume
the chair conformation as their most stable conformer; thus, the preferred conformation of the
dioxaspiran will have each respective ring in the chair conformation. The dioxaspiro compound can
exist in 3 conformations:
O
O
A B
O
O

  

Source: Andreana, Peter R. - Department of Chemistry, Wayne State University

 

Collections: Chemistry