Summary: CHM 7200 Organic Structures and Mechanisms Fall Term 2006
Problem Set 1: This problem set is now available at (www.blackboard.wayne.edu). It will be due
in class 7 days (09/15/05) from today (09/08/05). 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: Consider the conformations about the O-C(=C ) bond that are possible for methyl
vinyl ether. (Draw the two lone pairs on oxygen as substituents in appropriate Newman
a) What conformation would be preferred according to the , description of bonding?
b) What conformation would be preferred according to the bent bond description?
c) After answering parts a) and b), use the literature to find a paper on methyl vinyl ether
conformations. What do the experimental data tell you?
2. Problem: Construct a qualitative MO diagram showing how the -molecular orbitals in the
following molecules are modified by the addition of the substituent:
a) Vinyl fluoride, compared to ethylene
b) Acrolein, compared to ethylene
c) Acrylonitrile, compared to ethylene
d) Benzyl cation, compared to benzene
e) Propene, compared to ethylene
f) Fluorobenzene, compared to benzene