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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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
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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