Question

why di-tert-butyl ether cannot be prepared by williamson's synthesis ? explain.

Answer 1

To prepare di-tert butyl ether,  a  tertiary halide, tert-butyl halide is required.
However, Williamson synthesis does not occur with tertiary halides.
With tertiary halides, reaction undergoes elimination rather than substitution and forms alkene.

Answer 2

Answer:

Williamson's synthesis requires tert-butyl bromide and sodium tertiary butoxide to make di tert-butyl ether. The product obtained is isobutylene rather than ditertiary butyl ether because tert-butyl bromide is a 3°-alkyl halide that prefers to undergo elimination rather than substitution.

Explanation:

• We needed two reagents to make an ether from the Williamson synthesis: alkyl-halide and alkoxide.
• Alkyl halide is attacked by alkoxide in this reaction because alkoxide is more basic or a good attacker.
• So, if we try to make di-tert-butyl ether using Williamson synthesis, we'll need tert-butyl halide and tert-butyl-alkoxide as reagents.
• When tert-butyl halide combines with tert-butyl-alkoxide, however, it undergoes to produce 2-methylpropene and tert-butyl-alcohol as a byproduct.
• As a result, we can't use Williamson synthesis to make di-tert-butyl-ether.
• To make di-tert-butyl ether, tert-butyl bromide must be reacted with sodium tert-butoxide.
• Alkoxides are strong bases in addition to being nucleophiles.
• The elimination reaction occurs when they react with three alkyl halides.
• Elimination occurs when tert-butyl bromide combines with sodium tert-butoxide instead of substitution.
• Instead of di tert butyl ether, isobutylene is generated as a result of this elimination process.

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