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NAME (PRINT):
Last/Surname
STUDENT NO:
SIGNATURE:
1.
2.
3.
4.
5.
6.
7.
Total Marks
MARK
/15
/15
/15
/15
/20
/10
/10
/100
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1. Propose a synthesis for the following compound from phenol. For full marks you should
be able to complete the synthesis in 5 steps or less.
OH
O
NH2
15 Marks
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O
O
O
O
OH
OH
HO
O
O
OH
OH
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3. Suggest how you would synthesize compound B from A in 5 steps or less. You will lose
marks for using more than 5 steps.
O
H
15 Marks
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N
2.
Br
LiAlH4, THF
(1 equiv)
2. i) NaBH4, EtOH
ii) H3O+ (work up)
B
O
?
D
O
(1 equiv)
NEt3
?
E
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5. (i) Fill in the blanks (including reagents, solvents and reaction conditions)
in the following synthetic scheme. Note that a transformation may require more than one
step.
8 Marks
H
O
OH
O
H3O+
HO
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?
D
Continued on page 11
O
O
OH
H2N OH
(cat. H3O+)
OH
O
N
LiOH
H2O
Br
O
1. SOCl2, CH2Cl2
2. NH3
O
NH2
N
NH2
SOCl2
benzene, 80 oC
10 Marks
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7. Give 4 different sets of reaction conditions that will successfully facilitate the following
transformation shown below.
OH
10 Marks
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End of exam