S)-2-bromobutane reacts with H2O under the SN1 conditions to form two substitution products: one with the same relative configuration as the reactant (i. e. the product is (S)-2-butanol) and the other with the inverted configuration (i. e. the product is (R)-2-butanol). a) Explain how this happens (the formation of two stereoisomers – one with an inverted configuration and the other with a retained configuration). b) Which stereoisomer (configuration) will typically have a higher yield? Explain.
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.
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4. (S)-2-bromobutane reacts with H2O under the SN1 conditions to form two substitution products: one with the same relative configuration as the reactant (i. e. the product is (S)-2-butanol) and the other with the inverted configuration (i. e. the product is (R)-2-butanol).
a) Explain how this happens (the formation of two stereoisomers – one with an inverted configuration and the other with a retained configuration).
b) Which stereoisomer (configuration) will typically have a higher yield? Explain.
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