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. 1. 03 ΤΗ 2. (CH3)2S Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI 19 18 17 16 15 659 14 HBr Pd or Pt (catalyst) 13 12 11 10 mCPBA 1. Os04 2. H₂O2 CH3CO₂H (peroxyacid) 1. MCPBA 2. H₂O* HBr ROOR (peroxide) H₂O H₂SO4 HCI 1. BH3⚫THF 2. H₂O2, NaOH Br₂ 9 Bra H₂O BH3⚫THF Br2 Pd or Ni (catalyst) D₂ (deuterium) EtOH A B с ...OH OH D OH OH OH OH 'OH "OH 'OH

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
Section20.6: Sigmatropic Shifts
Problem 20.12P
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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.
ΤΗ
Pd or Pt (catalyst)
HBr
HBr
ROOR (peroxide)
H₂O
H2SO4
HCI
1. 03
2. (CH3)2S
Br2
CH₂OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
17
16
15
20 1 2
14
13
12 11 10
mCPBA
1. Os04
2. H₂O2
CH3CO₂H
(peroxyacid)
1. MCPBA
2. H₂O*
4
5
69
8
9
1. BH3.THF
2. H₂O2, NaOH
Br₂
Br₂
H₂O
BH3⚫THF
Br2
Pd or Ni (catalyst)
D₂ (deuterium)
EtOH
A
B
OH
OH
OH
OH
'OH
'OH
с
D
OH
OH
'OH
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. ΤΗ Pd or Pt (catalyst) HBr HBr ROOR (peroxide) H₂O H2SO4 HCI 1. 03 2. (CH3)2S Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI 17 16 15 20 1 2 14 13 12 11 10 mCPBA 1. Os04 2. H₂O2 CH3CO₂H (peroxyacid) 1. MCPBA 2. H₂O* 4 5 69 8 9 1. BH3.THF 2. H₂O2, NaOH Br₂ Br₂ H₂O BH3⚫THF Br2 Pd or Ni (catalyst) D₂ (deuterium) EtOH A B OH OH OH OH 'OH 'OH с D OH OH 'OH
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