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Which of the following ethers cannot be prepared by Williamson ether synthesis?

1. Methoxybenzene
2. Benzyl p-nitrophenyl ether
3. Methyl tert-butyl ether
4. Di-tert-butyl ether

Correct answer: Di-tert-butyl ether

Solution

Williamson synthesis needs an alkoxide to do SN2 on an alkyl halide. For di-tert-butyl ether both partners are tertiary, so the tert-butyl halide undergoes E2 elimination instead of substitution; it cannot be made this way.

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