ethyl sulfate is better o-methylating agent than ethyl halides why? suggest another substrate better than methyl halides for williamson synthesis.
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16.6 The Williamson Ether synthesis
The Williamson ether synthesis is an SN2 reaction in which an alkoxide ion is a nucleophile that displaces a halide ion from an alkyl halide to give an ether. The reaction occurs with inversion of configuration at chiral centers and can be limited by possible competing elimination reactions.
Intramolecular Williamson ether synthesis occurs at rates that depend on the number of atoms in the transition state. The rates are affected by the probability of the alkoxide approaching the carbon atom bearing the halide ion, as well as the strain of the resulting ring compound. The observed order of reactivity in terms of the ring size is 3 > 5 > 6 > 4.
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