Download Partial Periodic Table - Organic Chemistry at CU Boulder

CHEMISTRY 3331, Spring 2005
Professor Walba
Second Hour Exam, March 10
CU Honor Code Pledge: On my honor, as a University of Colorado at Boulder
Student, I have neither given nor received unauthorized assistance.
scores:
Name (printed): _________________________________
1)
Signature: ______________________________________
2)
Recitation TA Name: _____________________________
3)
4)
Recitation day and time: __________________________
This is a closed-book exam. The use of notes, models,
calculators, scratch paper, or any other paraphernalia will not be
allowed during the exam. Please put all your answers on the test.
Use the backs of the pages for scratch.
PLEASE read the questions very carefully!
1A
1
H
Partial Periodic Table
8A
2
He
2A
3
4
Li
Be
3A 4A 5A 6A 7A
5
6
7
8
9
10
B
C
N
O
F
Ne
11
12
Na Mg
13
14
15
Al
Si
P
16
S
17
18
Cl Ar
35
Br
53
Page 1 of 7
I
Name:
1) (25 pts) Give the single major organic product of each of the following reactions. Ignore stereochemistry
for this problem.
-
O
1) a) CH3O
O
Br
b)
a)
OCH3
2) a) NaOH, H2O, !
b) H3O+
OH
HBr
b)
C6H11Br
O
NaOH, H2O, Br2
NH2
c)
O
d)
O
NaBH4, CH3OH
OCH3
O
O
1)
H3C
O
O
H
e)
2) a) LiAlH4
b) H3O+ workup
Page 2 of 7
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Name:
2) (25 pts) Propose reagents for accomplishing the following transformations. More than one step may be
required. Ignore stereochemistry for this question.
OH
OH
a)
O
OH
b)
O
O
O
OCH3
c)
OH
OH
O
d)
OH
H
N
NH2
e)
Br
O
O
Br
Cl
N
Cl
Phenazepam
Page 3 of 7
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Name:
3) (25 pts) (a) Propose an arrow-pushing mechanism for this transformation.
O
1) NH2OH, mild H3O+
O
2) H2SO4, H2O
N
H
Page 4 of 7
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Name:
3 – continued
(b) When the diol 1 is allowed to react with p-toluenesulfonyl chloride in pyridine, the 2° tosylate 2 is
produced. In one short sentence, explain the regioselectivity of this reaction.
OTs
OH
HO
HO
TsCl, pyr
1
2
(c) Propose an arrow-pushing mechanism for the following transformation.
OTs
O
HO
CH3OH
Page 5 of 7
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Name:
4) (25 pts) (a) Propose a clean synthesis of ketone 1 using only alcohols containing 3 carbons or less as starting
materials. No other functional groups are allowed in the starting materials. You may use any inorganic
reagents you need.
O
1
(b) Propose reagents for converting ketone 1 to alkene 2. You may use ANY reagents you need (with any
number of carbon atoms) for this part of problem 4.
O
CH2
1
2
Page 6 of 7
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Name:
4 – continued
(c) Propose a synthesis of the ketoprofen isomer 2 starting with benzene, any organic starting material with
three carbons or less, and any inorganic regents you need.
CO2H
O
2 (rac)
Page 7 of 7
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