CHEMISTRY 314-01 MIDTERM # 1 – answer key September 29 ...
CHEMISTRY 314-01 MIDTERM # 1 – answer key September 29 ...
CHEMISTRY 314-01 MIDTERM # 1 – answer key September 29 ...
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O<br />
H H2NNH 2NNH 2<br />
KOH , heat<br />
CH2I2, Zn(Cu)<br />
ether<br />
8. (2 pts) Predict the major product of mono-nitration of the following compound:<br />
O<br />
Cl<br />
Cl<br />
OCH 3<br />
HNO 3<br />
H 2SO 4<br />
9. (4 pts) Suggest one example of each of the following (formulas please!):<br />
A. A Grignard reagent.<br />
CH3CH2MgCl<br />
B. A metal carbonyl.<br />
W(CO)6<br />
10. (4 pts) Using specific structures, suggest an example of each of the following:<br />
A. A Clemmensen reduction.<br />
B. Preparation of a lithium dialkylcuprate.<br />
2<br />
O<br />
Li + CuI<br />
Zn (Hg)<br />
HCl<br />
Δ<br />
ether<br />
O<br />
1) HC CNa , liq. NH3 2) H 3O +<br />
OCH 3<br />
CHCl 3<br />
KOH<br />
NO 2<br />
C. A carbene.<br />
O<br />
:C(OCH3)2<br />
HO<br />
Cl Cl<br />
D. A σ-donor, π-acceptor group.<br />
<strong>–</strong> B(OH)2<br />
CuLi + LiI<br />
11. Suggest a detailed synthetic sequence for the preparation of each of the following molecules, starting from the indicated<br />
compound, and using any other necessary reagents.<br />
A. (5 pts) 2-Chloro-4-nitrobenzoic acid, using benzene as a starting material (Assume you can separate o- and pisomers);<br />
Cl<br />
AlCl 3<br />
HNO 3<br />
H 2SO 4<br />
NO 2<br />
Cl 2<br />
FeCl 3<br />
NO 2<br />
Cl<br />
1) KMnO4 water/t-butanol<br />
2) HCl<br />
COOH<br />
Cl<br />
NO 2
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