Question 6 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. Pd or Pt (catalyst) HBr ROOR (peroxide) H₂O H₂SO4 HCI 1. BH, THF 2. H₂O2, NaOH Br2 Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI mCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) 18 17 16 15 14 13 2. (CH3)2S يرة 20 1 2 12 11 10 Br2 H₂O BH3.THF Br2 FIOH Pd or Ni (catalyst) D₂ (deuterium) A B 0 D ४.४ OH 8.8 "OH ४.४ "OH 3.8 OH OA B C D

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter15: Radical Reactions
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Question 6
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.
2. (CH3)2S
Br2
CH3OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
12
Pd or Pt (catalyst)
HBr
20 1 2
18
17
16
15
HBr
ROOR (peroxide)
H₂O
H2SO4
HCI
1. BH3⚫THF
6
2. H₂O2, NaOH
Br2
8.
12
11 10
Br2
14
13
MCPBA
1. OsO4
2. H₂O2
CH3CO₂H
(peroxyacid)
EtOH
deuterium)
Pd or Ni (catalyst)
A
B
H₂O
BH3⚫THF
0
D
H
OH
**
OH
OH
ď ď
OH
H
OH
ہی ہے
OH
H
OH
ď ď
'OH
Α
A B
C
D
Transcribed Image Text:Question 6 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. 2. (CH3)2S Br2 CH3OH 1.03 2. DMS KMnO4, NaOH cold HI 12 Pd or Pt (catalyst) HBr 20 1 2 18 17 16 15 HBr ROOR (peroxide) H₂O H2SO4 HCI 1. BH3⚫THF 6 2. H₂O2, NaOH Br2 8. 12 11 10 Br2 14 13 MCPBA 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) EtOH deuterium) Pd or Ni (catalyst) A B H₂O BH3⚫THF 0 D H OH ** OH OH ď ď OH H OH ہی ہے OH H OH ď ď 'OH Α A B C D
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