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. 2. DMS KMnO4, NaOH 1.03 2. (CH3)2S Br2 CH3OH 1. 03 ΖΗ Pd or Pt (catalyst) HBr 20 1 2 19 3 cold 18 HBr ROOR (peroxide) H₂O H2SO4 HCI 17 5 HI 16 6 15 mCPBA 14 13 9 12 11 10 1. OsO4 2. H2O2 CH3CO3H (peroxyacid) 1. MCPBA 2. H3O+ H₂O BH3 THF Br2 EtOH Pd or Ni (catalyst) D2 (deuterium) 8 7 1. BH3 THF 2. H2O2, NaOH Br2 Br2 A B C D OCH3 Br Br dddd Br OCH3 OCH3 Br OCH3 Br OCH3 Br OCH3 "Br OCH3 OCH3 Br
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. 2. DMS KMnO4, NaOH 1.03 2. (CH3)2S Br2 CH3OH 1. 03 ΖΗ Pd or Pt (catalyst) HBr 20 1 2 19 3 cold 18 HBr ROOR (peroxide) H₂O H2SO4 HCI 17 5 HI 16 6 15 mCPBA 14 13 9 12 11 10 1. OsO4 2. H2O2 CH3CO3H (peroxyacid) 1. MCPBA 2. H3O+ H₂O BH3 THF Br2 EtOH Pd or Ni (catalyst) D2 (deuterium) 8 7 1. BH3 THF 2. H2O2, NaOH Br2 Br2 A B C D OCH3 Br Br dddd Br OCH3 OCH3 Br OCH3 Br OCH3 Br OCH3 "Br OCH3 OCH3 Br
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.50P
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Transcribed Image Text: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.
2. DMS
KMnO4, NaOH
1.03
2. (CH3)2S
Br2
CH3OH
1. 03
ΖΗ
Pd or Pt (catalyst)
HBr
20
1
2
19
3
cold
18
HBr
ROOR (peroxide)
H₂O
H2SO4
HCI
17
5
HI
16
6
15
mCPBA
14
13
9
12 11 10
1. OsO4
2. H2O2
CH3CO3H
(peroxyacid)
1. MCPBA
2. H3O+
H₂O
BH3 THF
Br2
EtOH
Pd or Ni (catalyst)
D2 (deuterium)
8
7
1. BH3 THF
2. H2O2, NaOH
Br2
Br2
A
B
C
D
OCH3
Br
Br
dddd
Br
OCH3
OCH3
Br
OCH3
Br
OCH3
Br
OCH3
"Br
OCH3
OCH3
Br
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