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.
!["For each halogen, reactivities with four types of alkane C-H bonds are normalized to the reactivity of th
2-151 O
(tert-Butyl bromidej
90%
:
Less (primary)
0.06%mi
10%
Expected (statistical) ratio
C-H bond reactivity
Experimental ratio
More (tertiary)
99.94%
In Summary Increased reactivity goes hand in hand with reduced selectivity in radied.
stitution reactions. Fluorine and chlorine, the more reactive halogens, discriminate ba
the various types of C-H bonds much less than does the less reactive bromine (Table 3.
Relative Reactivities of the Four Types of Alkane C-H Bonds
in Halogenations
Table 3-6
F•
e Cl.
(25°C, gas)
C-H bond
Br
(150°C, g
(25°C, gas)
CH3-H
RCH-H"
R,CH-H
R;C-H
0.5
1
0.004
0.002
1.2
1
1
1.4
4
80
primary C-H bond.
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