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 19 18 17 16 Pd or Pt (catalyst) 20 1 2 HBr ROOR (peroxide) H₂O H₂SO4 HCI 6 1. BH3.THF 2. H₂O2, NaOH 12 11 10 MCPBA 1. Os04 2. H₂O2 CH3CO₂H (peroxyacid) 15 14 13 A B Pd or Ni (catalyst) D2 (deuterium) Br2 Br2 H₂O BH3⚫THF C D OH OH OH OH OH OH OH "OH "OH OH OH OH OH OH OH OH OH OH OH "OH A B ° C D

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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
19
18
17
16
Pd or Pt (catalyst)
20 1 2
HBr
ROOR (peroxide)
H₂O
12 11 10
MCPBA
1. Os04
2. H₂O2
CH3CO₂H
(peroxyacid)
15
14
13
A
B
H₂SO4
HCI
5
6
1. BH3.THF
2. H₂O2, NaOH
Pd or Ni (catalyst)
D₂ (deuterium)
Br2
Br2
H₂O
BH3⚫THF
C
D
...OH
OH
OH
OH
OH
OH
OH
"OH
"OH
OH
°
A
B
OH
OH
OH
OH
OH
C
OH
OH
OH
OH
OH
D
Transcribed Image Text: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 19 18 17 16 Pd or Pt (catalyst) 20 1 2 HBr ROOR (peroxide) H₂O 12 11 10 MCPBA 1. Os04 2. H₂O2 CH3CO₂H (peroxyacid) 15 14 13 A B H₂SO4 HCI 5 6 1. BH3.THF 2. H₂O2, NaOH Pd or Ni (catalyst) D₂ (deuterium) Br2 Br2 H₂O BH3⚫THF C D ...OH OH OH OH OH OH OH "OH "OH OH ° A B OH OH OH OH OH C OH OH OH OH OH D
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