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Question
Ethers can be prepared by Williamson synthesis in which an alkyl halide is reacted with sodium alkoxide. Di−tert−butylether can’t be prepared by this method. Explain.
Ethers can be prepared by Williamson synthesis in which an alkyl halide is reacted with sodium alkoxide. Di−tert−butylether can’t be prepared by this method. Explain.
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Solution
Williamson ether synthesis
In Williamson ether synthesis, alkyl halide is reacted with sodium alkoxide to form symmetrical or unsymmetrical ether.
The reaction involves an SN2 attack of an alkoxide ion on the alkyl halide.
The reason why di−tert−butyl ether can not be prepared by Williamson ether synthesis.
Di−tert−butyl ether can not be prepared by this method because if a tertiary butyl halide is used as a substrate, an elimination reaction takes place, resulting in the formation of an alkene. Due to steric hindrance, an SN2 reaction is not possible in this case.
Williamson ether synthesis
In Williamson ether synthesis, alkyl halide is reacted with sodium alkoxide to form symmetrical or unsymmetrical ether.
The reaction involves an SN2 attack of an alkoxide ion on the alkyl halide.
The reason why di−tert−butyl ether can not be prepared by Williamson ether synthesis.
Di−tert−butyl ether can not be prepared by this method because if a tertiary butyl halide is used as a substrate, an elimination reaction takes place, resulting in the formation of an alkene. Due to steric hindrance, an SN2 reaction is not possible in this case.
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