Show how the following ethers might be synthesized using (1) alkoxymercuration–demercuration and (2) the Williamson synthesis. (When one of these methods cannot beused for the given ether, point out why it will not work.) thyl cyclohexyl ether
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.
Show how the following ethers might be synthesized using (1) alkoxymercuration–
demercuration and (2) the Williamson synthesis. (When one of these methods cannot be
used for the given ether, point out why it will not work.)
thyl cyclohexyl ether
Ethyl cyclohexyl ether is formed by both reactions.
- Alkoxymercuration–demercuration: Cyclohexene reacts with Hg (OAc)2 + C2H5OH + NaBH4 and results in formation of ethylcyclohexyl ether.
- Williamson Synthesis: 1-bromocyclohexane reacts with sodium ethoxide then removal of sodium bromide will occur and form ethylcyclohexyl ether.
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