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Question
Illustrate the examples the limitations of Williamson's synthesis for the preparation of certain types of ethers.
Illustrate the examples the limitations of Williamson's synthesis for the preparation of certain types of ethers.
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Solution
(i) In Williamson's synthesis reaction for the preparation of ether, the alkyl halide used must be primary as tertiary halides readily undergo elimination with strong bases like C2H5ONa. This is be best understood by, taking the example of preparation of ethyl tertiary butyl ether. For which the reactants used are ethyl bromide and sodium tertiary butoxide, but not the tertiary butyl chloride and sodium ethoxide.
(ii) Aryl halides and vinyl halides cannot be used as substrates because they are less reactive in nucleophilic substitution.
(i) In Williamson's synthesis reaction for the preparation of ether, the alkyl halide used must be primary as tertiary halides readily undergo elimination with strong bases like C2H5ONa. This is be best understood by, taking the example of preparation of ethyl tertiary butyl ether. For which the reactants used are ethyl bromide and sodium tertiary butoxide, but not the tertiary butyl chloride and sodium ethoxide.
(ii) Aryl halides and vinyl halides cannot be used as substrates because they are less reactive in nucleophilic substitution.
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