Propose a synthetic route to produce the following transformation: ? A. HBr E. Na/NH, 1. H₂, Pd/C M. Br₂ OH B. NAOMe F. H₂O*, H₂SO4 J. NBS, hv N. 1.0₂ 2. DMS or H₂O C. KotBu G. xs HBr K. 1. Hg(OAC)2, H₂O 2. NaBH₂ O. 1.RCO₂H 2. H₂O* 1. R₂BH-THF D. 2. NaOH, H₂O2 H. 1. O 2. H₂O L. H₂, Lindlar's cat. P. OsO4, NMO

Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
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Chapter8: Addition Via Carbocation
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Propose a synthetic route to produce the following transformation:
?
A. HBr
E. Na/NH₂
1. H₂, Pd/C
M. Br₂
Options: O
Step 1
C
JOH
OH
B. NAOMe
F. H₂O*, H₂SO4
J. NBS, hv
N. 1.0, 2. DMS
or H₂O
ID
Step 2
G. xs HBr
K. 1. Hg(OAc)2, H₂O
2. NaBH4
C. KOIBU
0. 1.RC0₂H
2. H₂O*
Step 3
C
1. R₂BH-THF
D. 2. NaOH, H₂O₂
H. 1. 2. H₂O
L. H₂, Lindlar's cat.
P. OsO4, NMO
KNPBHA
D
Transcribed Image Text:Propose a synthetic route to produce the following transformation: ? A. HBr E. Na/NH₂ 1. H₂, Pd/C M. Br₂ Options: O Step 1 C JOH OH B. NAOMe F. H₂O*, H₂SO4 J. NBS, hv N. 1.0, 2. DMS or H₂O ID Step 2 G. xs HBr K. 1. Hg(OAc)2, H₂O 2. NaBH4 C. KOIBU 0. 1.RC0₂H 2. H₂O* Step 3 C 1. R₂BH-THF D. 2. NaOH, H₂O₂ H. 1. 2. H₂O L. H₂, Lindlar's cat. P. OsO4, NMO KNPBHA D
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