ORGANIC CHEMISTRY I (CHEM 2242) EXAM #6
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)
HBr,
peroxides
Br
2
,
h
ν
CH
3
CH
3
NBS,
h
υ
OH Br
H3CH3C
CH3
HBr,
RO-OR
NBS,
h
ν
H3CBr
CH3
CH3
H3CBr
QUESTION 2: Fill in the blanks. (3 points per blank)
NH
SOCl
2
H
3
C
CH
3
H
3
C
CH
3
H
3
C
CH
3
CH
3
O
H
3
C
CH
3
CH
3
CH
3
1.
2.
CH3
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)
H3C O H3C O
O
CH
3
h
ν
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)
OH H-Cl Cl
H3CCH3 H3CCH3
CH3 CH3
QUESTION 5: Propose a series of steps that convert the given starting material into the product shown. (6 points)
CH3 CH3
QUESTION 6: Propose a series of steps that convert the given starting material into the product shown.
(6 points)
OH multiple steps CH3
S
H
H3CH3C
O