Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers.

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asked Dec 26, 2017 in Chemistry by sforrest072 (157,439 points) 63 448 1279

Illustrate with examples the limitations of Williamson synthesis for the preparation of
certain types of ethers.

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answered Dec 26, 2017 by mdsamim (213,225 points) 5 10 22
selected Dec 26, 2017 by sforrest072
 
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The reaction of Williamson synthesis involves SN2 attack of an alkoxide ion on a primary alkyl halide.

But if secondary or tertiary alkyl halides are taken in place of primary alkyl halides, then elimination would compete over substitution. As a result, alkenes would be produced. This is because alkoxides are nucleophiles as well as strong bases. Hence, they react with alkyl halides, which results in an elimination reaction.

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