Organic Chemistry: CHEM 231B
Whittier College
Spring 2004
Problem Set #3
Due Thursday 4/8/2004 @ 5:00 p.m.
40 pts
1. Consider the following two reactions and experimental data (12 pts):
HCl / H2O
0 C
HCl / H2O
60C
GC Results
Time
5.21 min
5.35 min
5.45 min
5.90 min
% Area
73 %
negligible
1 %
26 %
GC Results
Time
5.21 min
5.35 min
5.45 min
5
.
9
0
m
i
n
% Area
30 %
28 %
2 %
4
0
%
1a. What are the identities of all of the products? (4 pts)
1b. Using mechanisms, structures, transition states and energy diagrams, explain the experimental results?
(8 pts)
2. Predict products for the following reactions: (12 pts)
1 drop of H2SO4?
OCH3
O
O
AlCl3?
NBS / hν?
O
O
O
O
?
?
show the mechanism for the first several steps
