2010 exam 1 organic chemistry
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8/6/2019 2010 Exam 1 Organic Chemistry
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Chem 346 Exam 1 - 2010
Question 1: / 15
Question 2: / 24
Question 3: / 16
Question 4: / 10
Question 5: / 10
Question 6: / 10
Question 7: / 15
TOTAL: / 100
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Chem 346 Exam 1 - 2010
1. Describe each of the following transformations as an oxidation, reduction, or neither,and explain your designation based on labeling the oxidation levels of the carbonsinvolved in the transformation. (3 points each)
A.C
N O
OH
Reaction classification:
B.O
CH 3
O
OH
Reaction classification:
C.N N OMe
CH 3 OH
Reaction classification:
D.
O
O
O
Cl
Cl
OH
Reaction classification:
E.
O
O
NH 2NH HO
OH
Reaction classification:
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Chem 346 Exam 1 - 2010
2. Predict the product(s) of the following transformations. (8 points each)
A.
NH2heat
(excess)
1.
2. MnO 23. Br 2, FeBr 3
O
O
B.
Cl
OH
NaNH 2C 8 H 8 O
C.
O
O Cl1. AlCl 3
2. H +, CH 3CH 2OH3. HNO 3 , cat. H 2SO 4
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Chem 346 Exam 1 - 2010
3. Provide reagents/conditions for executing the following synthetic sequence. You mayassume that you can separate ortho and para isomers. Each arrow should have one set of reaction conditions (this doesn’t include workups). (8 points each)
A.
O
O
HN
O
B.
HN
CH3
O
O
NH
O
(You may use/add these two compoundsat any stage in any order along the
synthetic sequence, but you must useboth.)
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Chem 346 Exam 1 - 2010
4. In the chlorination of aromatic compound naphthalene, two products arising fromregioselective substitutions are possible. Only one product is observed, however.Explain this regiochemical outcome by applying your conceptual understanding of thistype of reactivity. (10 points)
Cl2FeCl 3
ClCl
onlyproduct
notobserved
naphthalene
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Chem 346 Exam 1 - 2010
5. Provide a synthesis of compound A from diazonium salt B using reagents andconditions that we have discussed in lecture. You may assume that you can separateortho and para isomers. (10 points)
OH
Br
CN
from
N 2
A diazonium salt B
Cl
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Chem 346 Exam 1 - 2010
6. Provide an arrow-pushing mechanism for the following transformation. (10 points)
OH
O
O
O
H 2 SO 4
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Chem 346 Exam 1 - 2010
7. In the following transformation, an unusual product was formed in observableamounts. This product appears to involve the substitution of a ketone with a bromineatom. Provide an arrow-pushing mechanism that accounts for the formation of this
product from phenol A . (15 points – 5 points for step 1, 10 points for step 2)
OH
MeO OMe
CH 3
O1. Ac 2O, Et 3N2. Br 2
OAc
MeO OMe
Br Br
CH 3 CH 3
phenol A
O
O
OAc 2O:
Ac:O
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Chem 346 Exam 1 - 2010
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Chem 346 Exam 1 - 2010
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Chem 346 Exam 1 - 2010
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