Question 10 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 HI ZH 20 18 17 16 MCPBA 15 14 13 1. Os04 2. H₂O2 CH3CO₂H (peroxyacid) A B Pd or Pt (catalyst) 12 11 10 HBr ROOR (peroxide) H₂O H₂SO4 HCI 6 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF Br₂ EtOH с D Br OEt ď ď OEt "Br Br ""OEt OEt Br Α A B C D Br OEt OEt Br OEt Br Br OEt

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Chapter1: Chemical Foundations
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Question 10
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.
HBr
ROOR (peroxide)
H₂O
H2SO4
HCI
6
1. BH, THF
2. H₂O2, NaOH
Br2
Br2
CH₂OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
MCPBA
1. OsO4
2. H₂O₂
20
18
17
16
15
CH3CO₂H
(peroxyacid)
14
13
H2
Pd or Pt (catalyst)
12 11 10
Br2
H₂O
BH3⚫THF
Br₂
EtOH
A
B
с
D
Br
OEt
ď ď
OEt
Br
OEt
"Br
OEt
ск
Br
Br
OEt
ď ď
""OEt
Br
Br
OEt
Br
OEt
Α
A B
C
D
Transcribed Image Text:Question 10 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. HBr ROOR (peroxide) H₂O H2SO4 HCI 6 1. BH, THF 2. H₂O2, NaOH Br2 Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O₂ 20 18 17 16 15 CH3CO₂H (peroxyacid) 14 13 H2 Pd or Pt (catalyst) 12 11 10 Br2 H₂O BH3⚫THF Br₂ EtOH A B с D Br OEt ď ď OEt Br OEt "Br OEt ск Br Br OEt ď ď ""OEt Br Br OEt Br OEt Α A B C D
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