Question 18 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) Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O₂ 19 18 17 16 15 CH.COSH (peroxyacid) 14 MCPBA 13 Pd or F 20 1 2 12 11 10 Pd or Ni (catalyst) D₂ (deuterium) FIOH H₂O H₂SO4 HCI 1. BH, THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF A mig ОН ABCD OH с B D

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Question 18
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. BH3.THF
2. H₂O2, NaOH
Br2
Br2
CH₂OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
MCPBA
1. OsO4
2. H₂O₂
19
18
17
16
15
CH3CO₂H
(peroxyacid)
14
MCPBA
13
Pd or F
20 1 2 3
12 11 10
Pd or Ni (catalyst)
D₂ (deuterium)
FIOH
ABCD
A
с
OH
Br2
H₂O
BH3⚫THF
ОН
B
D
Transcribed Image Text:Question 18 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. BH3.THF 2. H₂O2, NaOH Br2 Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O₂ 19 18 17 16 15 CH3CO₂H (peroxyacid) 14 MCPBA 13 Pd or F 20 1 2 3 12 11 10 Pd or Ni (catalyst) D₂ (deuterium) FIOH ABCD A с OH Br2 H₂O BH3⚫THF ОН B D
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