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 CH₂OH 1.03 2. DMS KMnO4, NaOH cold IH MCPBA 1. OsO4 2. H₂O₂ 1.03 2. (CH3)2S 17 16 H₂ Pd or Pt (catalyst) HBr HBr ROOR (peroxide) Н20 H₂SO4 HCI 18 654 15 CH,COSH (peroxyacid) 14 13 20 1 2 12 11 10 4560 1. BH, THF 2. H₂O2, NaOH Br2 Br2 H₂O BH, THF Br₂ EtOH Pd or Ni (catalyst) D₂ (deuterium) 1. MCPBA 2. H₂O* A B C O D OH OH OH "OH

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Question 13
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
(CH3)2S
CH3OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
A
B
18
17
16
zu
2
Pd or Pt (catalyst)
HBr
19
20 1
HBr
ROOR (peroxide)
Н20
H2SO4
HCI
1. BH3⚫THF
2. H₂O2, NaOH
Br2
Br2
12
11 10
BH3⚫THF
H₂O
MCPBA
1. OsO4
2. H₂O2
CH3CO₂H
(peroxyacid)
MCPBA
15
14
13
C
A
D
Pd or Ni (catalyst)
D₂ (deuterium)
FIOH
B
с
D
OH
OH
OH
"OH
Transcribed Image Text:Question 13 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 (CH3)2S CH3OH 1.03 2. DMS KMnO4, NaOH cold HI A B 18 17 16 zu 2 Pd or Pt (catalyst) HBr 19 20 1 HBr ROOR (peroxide) Н20 H2SO4 HCI 1. BH3⚫THF 2. H₂O2, NaOH Br2 Br2 12 11 10 BH3⚫THF H₂O MCPBA 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) MCPBA 15 14 13 C A D Pd or Ni (catalyst) D₂ (deuterium) FIOH B с D OH OH OH "OH
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