Why is the Williamson synthesis not suitable for preparing t-butyl ethyl ether from sodium ethoxide

Q: What is the correct answer for CBSE12?

The correct answer is C. In the Williamson synthesis, if a tertiary alkyl halide (like t-butyl bromide) is used with a strong nucleophile and base (like sodium ethoxide), elimination reaction predominates over substitution. The alkoxide acts as a strong base, abstracting a proton and forming an alkene (2-methylpropene) instead of the ether.

Q: Why is the Williamson synthesis not suitable for preparing t-butyl ethyl ether from sodium ethoxide and t-butyl bromide?

The correct answer is C. In the Williamson synthesis, if a tertiary alkyl halide (like t-butyl bromide) is used with a strong nucleophile and base (like sodium ethoxide), elimination reaction predominates over substitution. The alkoxide acts as a strong base, abstracting a proton and forming an alkene (2-methylpropene) instead of the ether.

Q: What are the options for this CBSE12 question?

A. Sodium ethoxide is a weak nucleophile. · B. t-Butyl bromide is a primary alkyl halide. · C. Sodium ethoxide acts as a strong base, leading to elimination. · D. The reaction follows an SN1 mechanism, which is slow.

Question

Why is the Williamson synthesis not suitable for preparing t-butyl ethyl ether from sodium ethoxide and t-butyl bromide?

FirstInTest · Accepted Answer

In the Williamson synthesis, if a tertiary alkyl halide (like t-butyl bromide) is used with a strong nucleophile and base (like sodium ethoxide), elimination reaction predominates over substitution. The alkoxide acts as a strong base, abstracting a proton and forming an alkene (2-methylpropene) instead of the ether.

Answer

Sodium ethoxide is a weak nucleophile.

Answer

t-Butyl bromide is a primary alkyl halide.

Answer

Sodium ethoxide acts as a strong base, leading to elimination.

Answer

The reaction follows an SN1 mechanism, which is slow.

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