ETHERS
R-O-REthersEthers
C2H5-O-C2H5
Diethyl ether
Diethyl Ether
Check the “fine print”
PEROXIDES!!PEROXIDES!!
R-O-RO2
R-O-O-R RCH-OR
OOH
EXPLOSIVE
Ethyl methyl ether
methoxy group
CH3CHCH2CH3
OCH3
What is the name of this compound?
2-methyoxybutane
Ethylene Oxide
O
Tetrahydrofuran
OFuran
THF
Dioxane
Dioxin Dioxin
18-Crown-6
K+
X-
Williamson Ether SynthesisWilliamson Ether SynthesisWilliamson Ether SynthesisWilliamson Ether Synthesis
ROH
NaRONa
RONa + R’X ROR’
Nucleophilic Substitution Reaction
Why is this compound discussed on TV news?
How could you make this ether?
CH3-C-OH
CH3
CH3
CH3-C-O
CH3
CH3
KK
CH3IC-O-CH3
CH3
CH3
CH3
CH3OHNa CH3ONa
C CH2
CH3
CH3
Dimethyl sulfate
RONaCH3O-SO2-OCH3
R-O-CH3
Cleavage of EthersCleavage of Ethers
R-O-R 2 RBr HBr
CH3CH2
OCH3CH2
CH3CH2
OCH3CH2
H+
Br-
CH3CH2Br + CH3CH2OH
HBr
CH3CHCH2CH3
OCH3
EXAMPLE
CH3CHCH2CH3
Br
CH3Br+
HBr
EPOXIDESEPOXIDES
RCO3H
RO- + R’X R-O-R’
C CH
CH3
CH3H
Br
HO
Br2
H2O
C C
CH3H CH3
H
O
NaOH
RMgX + RCH2CH2OH
CH3OCH2CH2OH
CH3ONa +
CH3ONa +
?CH3OH
Unsymmetrical Epoxide
CH3ONa +CH3OH
C CH
H
OCH3
OH
CH3CH3
Basic
Least Hindered
CH3OH +
ACIDIC CONDITIONSACIDIC CONDITIONS
??H+
H+
C C
O
HH
CH3CH3
H
C C
OH
HH
CH3
CH3
C C
OH
HHCH3O
CH3
CH3
Most Substituted
CH2 CH2
O
CH2 CH2
O
H
+
OH H
CH2 CH2
OH
HO
H3O+
HCl
What is the product of this reaction?
HCl
C C
OH
HHCl
CH3
CH3
Summary
Nomenclature
Williamson Ether Synthesis
Cleavage of Ethers
Epoxides
RONa + R'X ROR' + NaX
ROR' + HBr RBr + R'Br
CH2CCH3
CH3O
CH3ONaCC
OCH3
HHHO
CH3CH3
CH2CCH3
CH3O
HClCC
OH
Cl HH
CH3CH3