Question 14 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 Pd or Pt (catalyst) HBr ROOR (peroxide) H₂O H2SO4 20 2 HCI 5 1. BH3.THF 2. H₂O2, NaOH 12 11 10 Br2 19 18 17 16 15 14 13 MCPBA 1. OsO4 2. H₂O₂ CH3CO₂H (peroxyacid) D₂ (deuterium) Pd or l Br2 H₂O BH3⚫THF A B 444 OH OH OH OH œ œœ "OH 'OH OH "OH OH OH с D 44 'OH OH œ œ OH OH OH OH OH ABCD

Chemistry
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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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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.
Question 14
Pd or Pt (catalyst)
19
18
17
16
20
2
HBr
ROOR (peroxide)
H₂O
H2SO4
HCI
5
1. BH3.THF
2. H₂O2, NaOH
13
12 11 10
Br2
Br2
CH₂OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
MCPBA
15
14
D₂
(deuterium)
Pd or l
A
B
Br₂
H₂O
BH3⚫THF
с
D
ď ď ď
d
OH
OH
OH
OH
œ œœ
"OH
OH
"OH
OH
OH
ď ď
'OH
OH
OH
de de
OH
OH
А
В
ABCD
Transcribed Image Text: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. Question 14 Pd or Pt (catalyst) 19 18 17 16 20 2 HBr ROOR (peroxide) H₂O H2SO4 HCI 5 1. BH3.THF 2. H₂O2, NaOH 13 12 11 10 Br2 Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA 15 14 D₂ (deuterium) Pd or l A B Br₂ H₂O BH3⚫THF с D ď ď ď d OH OH OH OH œ œœ "OH OH "OH OH OH ď ď 'OH OH OH de de OH OH А В ABCD
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