H₂O OH ď OH 2. Neutralizing work-up H₂O* TSOH, H₂O [a] A mCPBA H₂O* 1. BH-THF 2.H₂O₂, NaOH Bra H₂O 1. OsO. (catalytic) 2. NMO

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter22: Synthesis Workshop 2
Section: Chapter Questions
Problem 12CTQ
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Select the missing reagents in the following multistep synthesis. Ignore any inorganic
byproducts formed.
'H
Š
H
O
H₂O
OH
@
1. NaOH, heat
2. Neutralizing work-up
1
H3O+
O
TSOH, H₂O
O
H
a
A
B
C
D
E
HOCH2CH2CH₂OH
NaOH
HOCH2CH2CH₂OH
TSOH
HOCH2CH2CH₂OH
H₂O
TSOH, H₂O
CH₂OH(2 eq)
TSOH
Transcribed Image Text:Select the missing reagents in the following multistep synthesis. Ignore any inorganic byproducts formed. 'H Š H O H₂O OH @ 1. NaOH, heat 2. Neutralizing work-up 1 H3O+ O TSOH, H₂O O H a A B C D E HOCH2CH2CH₂OH NaOH HOCH2CH2CH₂OH TSOH HOCH2CH2CH₂OH H₂O TSOH, H₂O CH₂OH(2 eq) TSOH
O
H₂O
OH
O
OH
| a
Q
2. Neutralizing work-up
H3O+
TSOH, H₂O
O
A
B
C
D
E
mCPBA
H3O+
1. BH3-THF
2.H₂O2, NaOH
Br₂
H₂O
1. OsO4 (catalytic)
2. NMO
Transcribed Image Text:O H₂O OH O OH | a Q 2. Neutralizing work-up H3O+ TSOH, H₂O O A B C D E mCPBA H3O+ 1. BH3-THF 2.H₂O2, NaOH Br₂ H₂O 1. OsO4 (catalytic) 2. NMO
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Follow-up Question

The last reaction is either C, D, or E. 

NaOH
OH
OH
Q
<
1. BH3-THF
2.H₂O2, NaOH
HOCH2CH2CH2
OH
TSOH
A
B
C
D
E
NaOH
H₂O
HOCH₂CH2CH2OH
TSOH, H₂O
TSOH, H₂O
HgCl2, H2SO4
Transcribed Image Text:NaOH OH OH Q < 1. BH3-THF 2.H₂O2, NaOH HOCH2CH2CH2 OH TSOH A B C D E NaOH H₂O HOCH₂CH2CH2OH TSOH, H₂O TSOH, H₂O HgCl2, H2SO4
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