A Br₂ CH3OH 1.03 2. DMS KMnO4, NaOH cold HI mCPBA 1. OSO4 2. H₂O2 1.03 2. (CH3)2S 17 18 16 15 B 19 CH3CO3H (peroxyacid) 14 13 H₂ Pd or Pt (catalyst) HBr 20 1 1. МСРВА 2. H3O* 12 11 10 Pd or Ni (catalyst) 2 Br OCH 3 Looks for "Br OCH3 D2 (deuterium) 3 4 5 6 7 8 EtOH Br₂ C BH 3 THF Br HBr ROOR (peroxide) H₂O H₂SO4 ""OCH 3 HCI 1. BH 3 THF 2. H₂O2, NaOH Br₂ Br₂ H₂O D OCH3 Br + Br OCH3 OCH3 Br œ œ œ œ 'Br Br 'OCH 3 OCH 3

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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.

A
Br₂
CH3OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
mCPBA
1. OSO4
2. H₂O2
1.03
2. (CH3)2S
17
18
16
15
B
19
CH3CO3H
(peroxyacid)
14
13
H₂
Pd or Pt (catalyst)
HBr
20 1
1. МСРВА
2. H3O*
12 11 10
Pd or Ni (catalyst)
2
Br
OCH 3
Looks for
"Br
OCH3
D2 (deuterium)
3
4
5
6
7
8
EtOH
Br₂
C
BH 3 THF
Br
HBr
ROOR (peroxide)
H₂O
H₂SO4
""OCH 3
HCI
1. BH 3 THF
2. H₂O2, NaOH
Br₂
Br₂
H₂O
D
OCH3
Br
+
Br
OCH3
OCH3
Br
œ œ œ œ
'Br
Br
'OCH 3
OCH 3
Transcribed Image Text:A Br₂ CH3OH 1.03 2. DMS KMnO4, NaOH cold HI mCPBA 1. OSO4 2. H₂O2 1.03 2. (CH3)2S 17 18 16 15 B 19 CH3CO3H (peroxyacid) 14 13 H₂ Pd or Pt (catalyst) HBr 20 1 1. МСРВА 2. H3O* 12 11 10 Pd or Ni (catalyst) 2 Br OCH 3 Looks for "Br OCH3 D2 (deuterium) 3 4 5 6 7 8 EtOH Br₂ C BH 3 THF Br HBr ROOR (peroxide) H₂O H₂SO4 ""OCH 3 HCI 1. BH 3 THF 2. H₂O2, NaOH Br₂ Br₂ H₂O D OCH3 Br + Br OCH3 OCH3 Br œ œ œ œ 'Br Br 'OCH 3 OCH 3
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