Please predict the products for each of the following reactions.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter5: Stereochemistry At Tetrahedral Centers
Section5.SE: Something Extra
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Question 4
Please predict the products for each of the following reactions.
Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both).
If a mixture of enantiomers is formed, please draw all the enantiomers.
Br2
CH3OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
2. (CH3)2S
18
17
16
15
14
H₂
Pd or Pt (catalyst)
20 1 2
13
12 11 10
MCPBA
1. OsO4
2. H₂O2
CH3CO₂H
(peroxyacid)
MCPBA
A
४.४
A
B
C
D
B
H₂O
HBr
ROOR (peroxide)
H₂O
8
H2SO4
HCI
1. BH3.THF
2. H₂O2, NaOH
Br2
Br2
H₂O
BH3⚫THF
Br
Pd or Ni (catalyst)
D2 (deuterium)
EtOH
OH
OH
с
OH
D
OH
"OH
४.४
"OH
Transcribed Image Text:Question 4 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Br2 CH3OH 1.03 2. DMS KMnO4, NaOH cold HI 2. (CH3)2S 18 17 16 15 14 H₂ Pd or Pt (catalyst) 20 1 2 13 12 11 10 MCPBA 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) MCPBA A ४.४ A B C D B H₂O HBr ROOR (peroxide) H₂O 8 H2SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF Br Pd or Ni (catalyst) D2 (deuterium) EtOH OH OH с OH D OH "OH ४.४ "OH
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