Question 12 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 MCPBA 1. OsO4 2. H₂O₂ 19 18 17 16 15 CH3CO₂H (peroxyacid) 14 13 A OH фон кон OH A B C D Pd or Pt (catalyst) 20 1 2 ROOR HBr H₂SO4 HCI 8 12 11 10 Br FIOH D₂ (deuterium) B 1. BH3.THF 2. H2O2, NaOH Br2 Br2 H₂O BH3⚫THF с D OH OH OH "OH OH "OH OH OH OH OH OH OH 'OH OH "OH OH OH

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter9: Alkynes: An Introduction To Organic Synthesis
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Problem 46AP: A hydrocarbon of unknown structure has the formula C8H10. On catalytic hydrogenation over the...
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Question 12
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
20
2
19
18
17
16
15
ROOR
HBr
8
12 11 10
MCPBA
1. OsO4
2. H₂O₂
CH3CO₂H
(peroxyacid)
14
13
D₂ (deuterium)
H2SO4
HCI
1. BH3⚫THF
2. H₂O2, NaOH
Br2
Br2
H₂O
BH3⚫THF
Br
A
B
с
D
OH
OH
OH
OH
44444
OH
"OH
OH
OH
OH
OH
"OH
'OH
OH
"OH
OH
OH
OH
OH
chaine
OH
A
B
с
D
Transcribed Image Text:Question 12 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 20 2 19 18 17 16 15 ROOR HBr 8 12 11 10 MCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) 14 13 D₂ (deuterium) H2SO4 HCI 1. BH3⚫THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF Br A B с D OH OH OH OH 44444 OH "OH OH OH OH OH "OH 'OH OH "OH OH OH OH OH chaine OH A B с D
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