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.
Rearrangements can occur during the dehydration of 1° alcohols even though no 1° carbocation is formed—that is, a 1,2-shift occurs as the C − OH2+ bond is broken, forming a more stable 2° or 3° carbocation, as shown. Using this information, draw a stepwise mechanism that shows how CH3CH2CH2CH2OH is dehydrated with H2SO4 to form a mixture of CH3CH2CH = CH2 and the cis and trans isomers of CH3CH = CHCH3. We will see another example of this type of rearrangement in Section 18.5C.
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