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 1.0 2. DMS KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O₂ CH.COSH (peroxyacid) H₂O 17 16 15 14 20 12 11 10 deuterium) Pd or l (catalyst) Bra Pd or Pt (catalyst) HBr ROOR (peroxide) H₂O H₂SO4 HCI 1. BH, THF 2. H₂O2, NaOH Br2 H₂O BH, THF Br₂ 0 D A B ď ď ď ď OH Br OH Br OH OH Br ** 'Br OH 'Br OH ск Br A B C D

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter10: Oxidation And Reduction
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Question 8
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.
(CH3)2S
Br2
CH₂OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
Pd or Pt (catalyst)
HBr
ROOR (peroxide)
H₂O
20
1
3
18
4
17
16
H₂SO4
HCI
1. BH3.THF
2. H₂O2, NaOH
Br2
Br2
H₂O
BH3⚫THF
MCPBA
1. OsO4
2. H₂O2
CH3CO₂H
(peroxyacid)
MCPBA
15
14
13
9
12
11
10
Pd or Ni (catalyst)
D₂ (deuterium)
OCH
0
D
B
ď ď
OH
Br
ОН
Br
OH
'Br
ď ď
'OH
Br
'Br
OH
ce ca
OH
Br
Α
ABCD
Transcribed Image Text:Question 8 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. (CH3)2S Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI Pd or Pt (catalyst) HBr ROOR (peroxide) H₂O 20 1 3 18 4 17 16 H₂SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O BH3⚫THF MCPBA 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) MCPBA 15 14 13 9 12 11 10 Pd or Ni (catalyst) D₂ (deuterium) OCH 0 D B ď ď OH Br ОН Br OH 'Br ď ď 'OH Br 'Br OH ce ca OH Br Α ABCD
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