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. 2. (CH3)2S Bra CH₂OH 1.03 2. DMS KMnO4, NaOH cold 19 18 17 16 15 HI mCPBA 1. OsO4 2. H₂O₂ CHCO3H (peroxyacid) FBA 550 14 Pd or Pt (catalyst) 20 2 12 11 10 HBr ROOR (peroxide) H₂O H₂SO4 HCI 1. BH₁.THF 2. H₂O2, NaOH Br2 H₂O BH, THF EIOH Br₂ Pd or Ni (catalyst) D₂ (deuterium) Br₂ O A B с D A B Br H Br C Br D H "Br H ***Br

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter25: Enolate & Enol Nucleophiles
Section: Chapter Questions
Problem 15E
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Question 2
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
2. (CH3)2S
Pd or Pt (catalyst)
Br
20
19
18
17
16
15
HBr
ROOR (peroxide)
H₂O
H2SO4
HCI
1. BH3.THF
2. H₂O2, NaOH
Br2
Br2
12 11 10
H₂O
1.03
2. DMS
CH3OH
KMnO4, NaOH
cold
HI
MCPBA
1. Os04
2. H₂O₂
CH3CO₂H
(peroxyacid)
MCPBA
14
13
BH3⚫THF
Br2
Pd or Ni (catalyst)
D₂ (deuterium)
FIOH
A
B
Br
"H
Br
H
C
D
ď ď
H
"Br
O A
B
C
D
"Br
Transcribed Image Text:Question 2 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 2. (CH3)2S Pd or Pt (catalyst) Br 20 19 18 17 16 15 HBr ROOR (peroxide) H₂O H2SO4 HCI 1. BH3.THF 2. H₂O2, NaOH Br2 Br2 12 11 10 H₂O 1.03 2. DMS CH3OH KMnO4, NaOH cold HI MCPBA 1. Os04 2. H₂O₂ CH3CO₂H (peroxyacid) MCPBA 14 13 BH3⚫THF Br2 Pd or Ni (catalyst) D₂ (deuterium) FIOH A B Br "H Br H C D ď ď H "Br O A B C D "Br
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