ORGANIC CHEMISTRY I (CHEM 2242) EXAM #5
NOVEMBER 24, 2020 60 POINTS
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. (3 points per blank)
1
.
(
sia
)
2
BH
2
.
H
2
O
2
,
NaOH
CH3 Br
CH
3
CH3CH3
CH
3
NaH
Br
H3C H3C
CH
3
Cl
H
3
C
HBr
(2
equiv.)
CH
3
CH
3
CH
3
OH
H
2
SO
4
QUESTION 2: Fill in the blanks. (3 points per blank)
CH
3
CH
3
H
3
C
OH
H
2
SO
4
CH
3
CH
3
CH
3
1)
2)
H
2
,
Pd
CaCO
3
HBr
CH
3
OH
heat
CH
3
Alkyne
QUESTION 3: 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)
H2SO4
OH
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)
CH3 – CH3 Br Na+ OCH3
CH3 CH3
QUESTION 5: Propose a series of steps that convert the given starting material into the product shown. (6 points)
multiple
steps
HO
O
Br
Br
CH
3