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Q.

Which of the following cannot be made by using Williamson's synthesis?

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a

Di-tert-butyl ether

b

Methoxybenzene

c

Benzyl-p-nitrophenyl ether

d

Tert-butyl methyl ether

answer is D.

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Detailed Solution

In Williamson's synthesis, best results obtained if the alkyl halide is 1°, in case of 2° alkyl halide, elimination competes over substitution. If a 3° alkyl. Halide is used, an alkene is the major product and no ether is formed.

Considering fourth option as di-tert butyl ether. It cannot be prepared by the method as it require 3° halide which give elimination product.

Diphenyl ether is also not prepared by the same method as there is resonance between the unshared pair of electrons of halogen and benzene ring.

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Which of the following cannot be made by using Williamson's synthesis?