CH3 CH3 1. PBr3/pyridine C. RI "OH H "OCH3 R H. same configuration as the alcohol 2. СH0 CH3 CH3 1. TsCl/pyridine R "OH H CH3O" 2. CH;0¯ R H configuration opposite that of the alcohol
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.
Explain why the ether obtained by treating an optically active alcohol with PBr3 in pyridine followed by sodium methoxide has the same configuration as the alcohol, whereas the ether obtained by treating the alcohol with tosyl chloride followed by sodium methoxide has a configuration opposite that of the alcohol.
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