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Ethers
Unit 7
Ethers!
 Ether
– organic compounds
where two alkyl or aryl
groups joined singly with
an oxygen atom
 R-O-R’
R-O-Ar
Ar-O-Ar
Ethers
 Symmetrical
ethers – 2
identical groups bonded to
the oxygen
 Unsymmetrical ethers – two
different groups bonded to
the oxygen
Nomenclature
 Name
the attached groups
followed by ether
 C-O-C-C Methyl ethyl ether (unsymm)
 C-C-O-C-C
Diethyl ether (symm)
 C-C-O C-C-C-C-O-
Preparation of Ethers
1.
Symmetrical ethers = dehydrate alcohols
2R-OH H2SO4 R-O-R + H2O
Form dipropyl ether
2 C-C-C-OH H2SO4 C-C-C-O-C-C-C + H2O
2CH3CH2CH2OH H2SO4 CH3(CH2)2O(CH2)2CH3
+ H2O
Preparation of Ethers
2. Unsymmetrical ethers = Williamson
Synthesis
Alkyl halide + alcohol salt  ether + metal halide
RX + RO-M+  ROR’ + MX
Preparation of Ethers - Williamson


If there are 2 alkyl groups, the
smaller alkyl group is the halide and
the larger is the metal salt
If there is an alkyl group and a
phenyl, the phenyl is ALWAYS the
salt 
Preparation of Ethers - Williamson
Form methyl ethyl ether (name reactants)
CH3Cl + (C-C-O-)Na+  C-O-C-C + NaCl

CH3Cl+(CH3CH2O-)Na+  CH3OCH2CH3+NaCl
Methyl chloride + sodium ethoxide
(chlormethane)
Preparation of Ethers - Williamson

Form propyl phenyl ether
Reactions of Ethers



Ether + hydrogen halide  alcohol +
alkyl halide
ROR + HX  ROH + RX
If either had two alkyl groups, the
smaller one forms the alcohol. If it is a
phenyl and an alcohol, the phenyl forms
phenol
Reactions of Ethers



React ethyl phenyl ether w/HBr
C-C-O+ HBr  C-C-Br + -OH
React methy phenyl ether w/HF