Chemistry Exam Worksheet - Chemistry 61, Dr. M.t. Crimmins, The University Of North Carolina At Chapel Hill Page 4

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Syntheses. Give reagents to show how to synthesize the compounds on the right from the compounds
on the left. They may require more than one step. (4 pts each)
21.
1. n-BuLi, I–CH
CH
CH
O
2
2
3
H
C
C
H
H
C
C
CH
CH
CH
3
2
2
3
2. H
O, H
SO
, HgSO
2
2
4
4
22.
1. m-CPBA
OH
OH
+
2. H
O, H
2
V.
Mechanisms. Give a stepwise, detailed mechanism with arrows and intermediates for the
following reactions. (5 points each)
23.
CH
CH
CH
3
3
3
H
SO
2
4
H
C
C
C
CH
H
C
C
C
CH
3
3
3
3
heat
O
CH
OH
OH
3
+
H
CH
CH
3
3
H
C
C
C
CH
3
3
+
HO
O
H
H
CH
3
CH
CH
3
3
H
C
C
C
CH
3
3
H
C
C
C
CH
3
3
+
+
O
CH
3
HO
H
H
O
2
– 4 –

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