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.

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
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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 10
Pd or Pt (catalyst)
20 1 2
HBr
ROOR (peroxide)
H₂O
H₂SO4
HCI
1. BH3.THF
2. H₂O2, NaOH
12 11 10
Br2
Br2
CH₂OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
MCPBA
1. OsO4
2. H₂O₂
19
18
17
16
CH3CO₂H
(peroxyacid)
15
14
MCPBA
13
H3O+
Br2
H₂O
BH3⚫THF
FIOH
Pd or Ni (catalyst)
A
Br
B
OEt
с
Br
D
OEt
ď ď ď ď
OEt
Br
+
'Br
OEt
"OEt
Br
+
de de de d
"OEt
Br
OEt
Br
OEt
***Br
Α
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 10 Pd or Pt (catalyst) 20 1 2 HBr ROOR (peroxide) H₂O H₂SO4 HCI 1. BH3.THF 2. H₂O2, NaOH 12 11 10 Br2 Br2 CH₂OH 1.03 2. DMS KMnO4, NaOH cold HI MCPBA 1. OsO4 2. H₂O₂ 19 18 17 16 CH3CO₂H (peroxyacid) 15 14 MCPBA 13 H3O+ Br2 H₂O BH3⚫THF FIOH Pd or Ni (catalyst) A Br B OEt с Br D OEt ď ď ď ď OEt Br + 'Br OEt "OEt Br + de de de d "OEt Br OEt Br OEt ***Br Α ABCD
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