ORGANIC CHEMISTRY I (CHEM 2242) EXAM #4
BEFORE YOU BEGIN, TAKE A MOMENT TO WRITE DOWN HERE TWO THINGS ON THIS EXAM
THAT YOU ARE CONFIDENT THAT YOU UNDERSTAND:
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**TAKE A BREATH**
QUESTION 1: Fill in the blanks in the following reactions. Include stereochemistry when relevant. (4 points per blank)
O
1)
O
3
2)
(
CH
3
)
2
S
H + O
H
3
C
CH
3
OH
Br
CH
3
+
S
H
3
C
P
H
CH
3
H
3
C
CH
3
Br
CH
3
+
H
N
CH
3
1)
BH
3
*
THF
2)
H
2
O
2
,
NaOH
CH3
1
.
Hg(OAc)
2
,
H
2
O
2
.
NaBH
4
CH3
OH
CH3
(
CH
3
)
2
NH
H3CCH3
I
CH3
OH
H3CCH3
I
Br H2, Pt
1)
H3C
CH3 2) CH3CH2OH
QUESTION 2: Which of the following products cannot be made from this starting alkene? (2 points)
H3C starting alkene | H3C OH OH A) | H3C Br B) | Br | H3C H C) | OH | H3C OH Br D)
|
QUESTION 3: Fill in the reagents and conditions for each step.
(3 points per step)
H3C H3C
CH3
CH3
Cl
O
OH
CH3
QUESTION 4: Draw a mechanism for the following transformation that shows the flow of electrons leading to the product. Show any intermediates in the mechanism. (6 points)
H3CH3C
Br OCH3
CH
3
OH
QUESTION 5: Draw a mechanism for the following transformation that shows the flow of electrons leading to the product. Show any intermediates in the mechanism.
(6 points)
H3C
H3C OH
Br2, H2OBr
QUESTION 6: Identify the leaving group and the nucleophile in the following SN2 reaction. (5 points)
H
N
O
O
CH
3
H3C CHN 3 3C CH3
CH
H3CH3C3