03 CHalas H₂ Pd or Pt (catal HBr HBr ROOR (peroxide) H₂O H₂SO4 20 1 2 HCI 3 18 1. BH3 2. H₂O2 Br2 14 13 12 11 10 P Br2 Ha

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 21AP
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А
A B C
D
Question 3
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.
1.03
2. (CH3)2S
Br2
CH₂OH
12
Pd or Pt (catalyst)
HBr
ROOR (peroxide)
Н20
H2SO4
HCI
1. OsO4
2. H₂O2
CH3CO₂H
(peroxyacid)
MCPBA
CFBA
2. H3O+
ТСРВА
HI
KMnO4, NaOH
cold
2. DMS
19
18
17
16
15
14
13
12 11 10
BH3⚫THF
Br
Pd or Ni (catalyst)
D₂ (deuterium)
EtOH
1.03
20 1 2
1. BH3.THF
2. H₂O2, NaOH
Br2
Br2
H₂O
A
B
Br
Br
C
Br
D
αα
Br
""Br
αα
Br
"Br
.... Br
Transcribed Image Text:А A B C D Question 3 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. 1.03 2. (CH3)2S Br2 CH₂OH 12 Pd or Pt (catalyst) HBr ROOR (peroxide) Н20 H2SO4 HCI 1. OsO4 2. H₂O2 CH3CO₂H (peroxyacid) MCPBA CFBA 2. H3O+ ТСРВА HI KMnO4, NaOH cold 2. DMS 19 18 17 16 15 14 13 12 11 10 BH3⚫THF Br Pd or Ni (catalyst) D₂ (deuterium) EtOH 1.03 20 1 2 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 H₂O A B Br Br C Br D αα Br ""Br αα Br "Br .... Br
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