1
CH341-01/CH540, Exam 5, Fall 2009
______________________________________
Name
This exam consists of several parts of unequal difficulty. Look over the whole exam right now, and start
on something you know well. If you don’t know something, skip it, and come back to it later. Use your
time wisely.
Keep Your Eyes On Your Own Paper!
Grading Summary
Page 2. _______________ (20)
Page 5. _______________ (12)
Page 3. _______________ (30)
Page 6. _______________ (12)
Page 4. _______________ (20)
Page 7. _______________ (6 +)
Total ___________________
A Partial Periodic Table of the Elements
1A
IIA
IIIB
IVB
VB
VIB
VII
B
VIII
IB
IIB
IIIA
IVA
VA
VIA
VII
A
1
H
VIII
A
2
He
1.01
4.00
3
Li
4
Be
5
B
6
C
7
N
8
O
9
F
10
Ne
6.94
9.01
10.8
12.0
14.0
16.0
19.0
20.2
11
Na
12
Mg
13
Al
14
Si
15
P
16
S
17
Cl
18
Ar
23.0
24.3
27.0
28.1
31.0
32.1
35.5
40.0
19
K
20
Ca
31
Ga
32
Ge
33
As
34
Se
35
Br
36
Kr
39.1
40.1
69.7
72.6
74.9
79.0
79.9
83.8
37
38
49
50
51
52
Te
53
I
54
128
127
21
22
23
24
25
26
27
28
29
30
39
40
41
42
43
44
45
46
47
48
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1. (20) Give IUPAC names for the following structures. Use R, S, E, or Z, when needed.
a.
O
H2N
OH
HO
b.
H3C
N
CH3
H3C
CH3
CH3
c.
NH2
CH3CH2
CH2CH3
d. Draw the structure of tripropylamine.
3
2. (30) Draw the major organic product of each of the following reactions. If no reaction will occur,
write “No Reaction.”
a.
O
SOCl2
CH3
HO
heat
b.
H
O
200 °C
N
CH3
HO
c.
+
CH3
O
OH
+
CH3
HO
d.
H+ (cat.)
O
CH3
e.
Cl
+
NH2
+
H2N
CH2CH3
(excess)
CH3
f.
H2C
NO2
NaBH3CN
CH3OH, HCl
pH = 6
H+ (cat.)
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3. (20) Supply the needed reagents and experimental conditions to accomplish each of the following
transformations. More than one step may be required in some cases.
a.
C
N
CH2 NH2
b.
O
H3C
OH
H3C
c.
OH
H
N
O
d.
O
O
OH
O
OH
O
O
Draw the structure of the “polymer” that would be formed if two molecules of each of the following
materials reacted with each other.
H2N
2
O
NH2
+
O
heat
2
HO
OH
5
4. (12) Write acceptable arrow-pushing mechanisms for the following reactions.
a.
O
O
H+ (cat.), heat
C
C
+ H2O
+ HO CH3
H3C
O CH3
H3C
OH
b.
Na
H
+
N
H3C
CH3
+
C
CH3
H
H
N
B
-
H
H
H2O
H3C
C
H
CH3
+ BH3 + NaOH
CH3
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5. (12) How would you synthesize the following products from the indicated starting materials? You do
not need to draw the mechanisms. If you show intermediate structures, I can more easily give you partial
credit.
Product
a.
Starting Material
CH2CH3
O
H2N
b.
C
OH
OH
O
C
H3C
CH2
OH
H3C
CH2
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6a. Rank the following from highest (#1) to lowest (#3) in boiling point. Briefly explain your reasoning.
CH3
CH3
O
H3C
H3C
H3C
OH
NH2
OH
6b. Rank the following from highest (#1) to lowest (#3) in base strength.
NH2
Na
+
CH3
O H
-
H3C
NH2
Bonus: When starting material A, below, is treated with excess H2, in the presence of Pd and an acid
catalyst, product B is formed. A series of reaction occur to get from A to B. Draw the sequence of
reactions that occurs. You do not need to draw the mechanisms.
O
H
N
Excess H2, Pd (cat.)
H+ (cat.)
C
"A"
N
"B"