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Answer Key for Problem Set 1 1. 2. 3. 4.
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Answer Key for Problem Set 1 1. 2. 3. 4.
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Answer Key for Problem Set 1. 1. C. C. H. NaNH2. NH3(l), 33oC. C. C: O. 1. 2. H3O+. OH. OH under harsh acid conditions. 2. Br. OH. 1 eq BuLi. Et2O. Br. OLi.
Answer Key for Problem Set 1
1. C
C
OH
H C
NaNH2 NH3 (l),
C: 1.
33oC
O
2. H3 O+
OH under harsh acid conditions
2.
Br
Br 1 eq BuLi
Li 1 eq BuLi
Et2 O
O
Et2 O
OH
OLi
1.
2. NH4Cl
OH
OLi
OH (extra credit for the right stereochemistry)
3. NC
Et2CuLi I
4. CH2I2 Zn-Cu
THF, 0oC
NC
Et
5. Br Br (CH3)2CuLi
CHBr3 OH-
Et2O
6. a) Br
H
-
Cu
Cu
2
2Br
H
b) Br
-
Cu
Cu
2
7. H
H Li2 2CuCN THF, 0oC
O
OH
2Br
H
8. H
H
+
Br
1 eq BuLi
H
Li
OSiEt3 +
Br
1 eq BuLi Li
H2, Pd/CaCO3
OSiEt3
quinoline OSiEt3 CH2 I2 , Zn-Cu
TBAF OH
OSiEt3
OSiEt3
Na NH3 OSiEt3
CH2 I2 , Zn-Cu
TBAF OH
OSiEt3
9. a) H
+ 1 eq BuLi
H
H
Li
O H
Li
OH H
+
MeO
MeO
b) O
OCH3
HO Li
+
c) MgBr
I +
+
10. Br
1.
2CuCN
Li2
2. CH2I2, Zn-Cu
Br
2CuCN
2. CH2I2, Zn-Cu
Li2
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