Transcript Ethers

ETHERS
Ethers
R-O-R
C2H5-O-C2H5
Diethyl ether
Diethyl Ether
Check the “fine print”
PEROXIDES!!
R-O-R
O2
R-O-O-R
OOH
RCH-OR
EXPLOSIVE
CH3CH2OCH3
Ethyl methyl ether
-OCH3
methoxy group
What is the name of this compound?
OCH3
CH3CHCH2CH3
2-methyoxybutane
O
CH2
CH2
Ethylene Oxide
O
Furan
O
Tetrahydrofuran
THF
O
O
Dioxane
Cl
O
Cl
Cl
O
Cl
Dioxin
18-Crown-6
XK+
Williamson Ether Synthesis
Na
RO
H
RONa + R’X
RONa
ROR’
Nucleophilic
Substitution Reaction
Why is this compound
discussed on TV news?
CH3
CH3 C-O-CH3
CH3
How could you make this ether?
CH3
CH3 C-O-CH3
CH3
CH3
CH3-C-OH
CH3
CH3I
K
CH3
CH3-C-O
CH3
CH3
CH3 C-O-CH3
CH3
K
CH3OH
Na
CH3ONa
CH3
C Cl
CH3
CH3
CH3
C
CH3
CH2
O
CH3-O-S-O-CH3
O
Dimethyl sulfate
CH3O-SO2-OCH3
RONa
R-O-CH3
Cleavage of Ethers
HBr
R-O-R
2 RBr
CH3CH2
HBr
O
CH3CH2
CH3CH2 +
O H
CH3CH2
Br -
CH3CH2Br + CH3CH2OH
EXAMPLE
OCH3
HBr
CH3CHCH2CH3
Br
CH3CHCH2CH3
+
CH3Br
EPOXIDES
C
C
O
RCO3H
C
C
+ R’X
RO
R-O-R’
O
Br
C
O
C
C
C
CH3
H
C
C
NaOH
H
CH3
Br2
CH3
H
C
H2O
HO
CH3
H
C
C
O
Br
C
H
CH3
H
CH3
O
RMgX +
CH2
CH2
RCH2CH2OH
O
CH3ONa +
CH2
CH2
CH3OCH2CH2OH
Unsymmetrical Epoxide
O
CH3ONa +
CH3OH
CH3
CH3
C
?
C
H
H
Basic
O
CH3ONa +
CH3
CH3
OH
CH3
CH3
C
C
C
C
H
H
CH3OH
H
H
OCH3
Least Hindered
ACIDIC CONDITIONS
O
CH3OH
H+
+
CH3
CH3
?
C
C
H
H
H+
O
CH3
CH3
C
H
C
O
H
H
CH3
CH3
C
C
H
H
OH
CH3
CH3
CH3
CH3
CH3O
C
C
H
H
OH
C
C
H
H
Most Substituted
H
H3O+
O
CH2
O+
CH2
CH2
O
H
H
OH
CH2
HO
CH2
CH2
What is the product of this reaction?
O
CH3
CH3
C
HCl
C
H
H
O
CH3
CH3
C
C
HCl
H
H
CH3
CH3
Cl
OH
C
C
H
H
Summary
Nomenclature
Williamson Ether Synthesis
RONa + R'X
RO R' + NaX
Cleavage of Ethers
ROR' + HBr
RBr + R'Br
Epoxides
CH3
CH3
CH3
CH3
HO
O
C
CH2
O
C
CH3ONa
CH3
CH3
HCl
CH2
H
H
C
C
OCH 3
CH3
CH3 C
Cl
OH
C
H
H