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 BOH 1.03 2. DMS KMnO4, NaOH cold HI 20 Pd or Pt (catalyst) HBr ROOR (peroxide) Н2О H₂SO4 MCPBA 1. Os04 2. H₂O2 CH3CO₂H (peroxyacid) 17 16 15 MCPBA MCPBA H3O+ 14 18 12 11 10 D₂ (deuterium) Pd or Ni (catalyst) Br2 H₂O BH3⚫THF Bra HCI 1. BH3.THF 2. H₂O2, NaOH Br2 A B 0 D Br ď ď OH Br + Br OH Br "OH Br "Br OH ď ď ď ď "OH 'Br OH Br A B C D

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
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Chapter9: Alkynes: An Introduction To Organic Synthesis
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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.
Br2
(CH3)2S
CH₂OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
Pd or Pt (catalyst)
HBr
ROOR (peroxide)
H₂O
H2SO4
HCI
20
18
17
16
15
14
12 11 10
1. BH, THF
2. H₂O2, NaOH
Br2
Br2
MCPBA
1. Os04
2. H₂O2
CHCO3H
(peroxyacid)
МСРВА
MCPBA
H3O+
D₂ (deuterium)
Pd or Ni (catalyst)
H₂O
BH3⚫THF
Br₂
A
Br
B
ď ď
OH
Br
+
Br
OH
0
Br
"OH
Br
D
OH
"Br
OH
ď ď ď ď
"OH
"Br
OH
Br
A
B
C
D
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. Br2 (CH3)2S CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI Pd or Pt (catalyst) HBr ROOR (peroxide) H₂O H2SO4 HCI 20 18 17 16 15 14 12 11 10 1. BH, THF 2. H₂O2, NaOH Br2 Br2 MCPBA 1. Os04 2. H₂O2 CHCO3H (peroxyacid) МСРВА MCPBA H3O+ D₂ (deuterium) Pd or Ni (catalyst) H₂O BH3⚫THF Br₂ A Br B ď ď OH Br + Br OH 0 Br "OH Br D OH "Br OH ď ď ď ď "OH "Br OH Br A B C D
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