Preparation
u Ether u u
Williamson Ether Synthesis (from ROH and RX) Alkoxymercuration - Demercuration (of alkenes) Expoxidation (of alkenes by peracids)
A. Williamson Ether Synthesis
u
1 R-X + R'-OO
R-O-R' + XSN2
Br O
+
ethoxide
SN2
O
+ Br
+
O
H3C
I
+ I
Alkyl halide must be primary for the Williamson Ether Synthesis
make alkoxides by deprotonation of alcohols
OH
+
NaH (NaNH2) (Na)
O
Na
+ H2
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B. Alkoxymercuration - Demercuration of Alkenes
u
Markovnikov addition of H & to OR alkenes
O
1) Hg(OAc)2, CH3CH2OH 2) NaBH4 1)
H3C O-CH2CH3 CH2 Hg(OAc) H3C CH2 H
2)
isopropyl ethyl ether
1) Hg(OCCF3)2, CH3OH 2) NaBH4
O-CH3 CH3
C. Epoxidation of Alkenes by Peracids
u u
mCPBA Oxidation of Alkenes to Epoxides MMPP Oxidation of Alkenes to Epoxides
mCPBA
O
O Cl O O H
m-clo...