Whittier College
Organic Chemistry: CHEM 231A
Problem Set # 3
40 Points Total
Due 12:00 pm on October 30, 2003
1. Given the following reaction: (8 points)
Br
K
C
N
/
S
o
l
v
e
n
t
Solvent
Methanol
DMF
Rate
60 minutes
1
0
m
i
n
u
t
e
s
1a. What is the product for this reaction? (1 pt)
1b. What is the mechanism for this reaction? (2 pts)
1c. Provide an explanation for the difference in rate data. (3 pts)
1d. If the starting material is optically pure, would the product of the reaction also be optically pure?
Explain. (2 pts)
2. Consider the following reactions: Will the reaction occur as drawn? If not, draw the more favorable
product? In either case, explain your answer. (12 pts = 4 pts each)
2a.
2b.
Br
NaCN / Ethyl Acetate
N
HO
N
Optically PureRacemic
2c.
Optically PureOptically Pure
Br
O
diethyl ether
O
1.
O
S
O
CH3
Cl
pyridine
2. HN(CH3)2
