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 IH MCPBA 1. OsO4 2. H₂O₂ 1.03 2. (CH3)2S 17 16 H₂ Pd or Pt (catalyst) HBr HBr ROOR (peroxide) Н20 H₂SO4 HCI 18 654 15 CH,COSH (peroxyacid) 14 13 20 1 2 12 11 10 4560 1. BH, THF 2. H₂O2, NaOH Br2 Br2 H₂O BH, THF Br₂ EtOH Pd or Ni (catalyst) D₂ (deuterium) 1. MCPBA 2. H₂O* A B C O D OH OH OH "OH
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
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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.
Br2
(CH3)2S
CH3OH
1.03
2. DMS
KMnO4, NaOH
cold
HI
A
B
18
17
16
zu
2
Pd or Pt (catalyst)
HBr
19
20 1
HBr
ROOR (peroxide)
Н20
H2SO4
HCI
1. BH3⚫THF
2. H₂O2, NaOH
Br2
Br2
12
11 10
BH3⚫THF
H₂O
MCPBA
1. OsO4
2. H₂O2
CH3CO₂H
(peroxyacid)
MCPBA
15
14
13
C
A
D
Pd or Ni (catalyst)
D₂ (deuterium)
FIOH
B
с
D
OH
OH
OH
"OH"
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