Chemistry Exam Worksheet - Chemistry 61, Dr. M.t. Crimmins, The University Of North Carolina At Chapel Hill Page 2

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8.
1. n-BuLi
H C C H
H C C CH
CH
OH
2
2
2.
H
C
CH
2
2
O
9.
CN
+ –
I
Na
CN
H
C
3
H
C
3
10.
CH
CH
2
3
C
O C
CH
OH
3
H
C
CH
3
3
CH
3
H
SO
2
4
11.
H
1. Br
, H
O
2
2
O
2. NaH
H
12.
Br
Br
2
H
C C C CH
3
3
H
C C C CH
3
3
Br
13. Indicate whether the following reactions are more likely to proceed by an E1, E2, SN1 or SN2
mechansim. (2 points each)
CH
CH
2
3
–
CH
CH
S
3
2
H
C
C
Br
a.
S
2
3
N
H
Br
E2
– +
CH
O
Na
3
C
CH
b.
3
CH
3
OH
E1
H
PO
3
4
c.
C
H
heat
CH
3
OCH
S
1
HI
3
N
d.
C
CH
3
25 °C
CH
3
II.
Multiple Choice: Circle the best answer (only one). (3 points each)
– 2 –

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