Pick an ether which cannot be prepared by direct Williamson's synthesis:

(C H_{3})_{3} C - O - C_{2} H_{5}

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C H_{3} C H_{2} C H_{2} - O - C H_{2} C H_{2} C H_{3}

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P h - O - C H_{2} C H_{3}

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C H_{3} C H = C H - O - C H = C H_{2}

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Solution

The correct option is D $C H_{3} C H = C H - O - C H = C H_{2}$
The Williamson ether synthesis is an $S_{N} 2$ reaction in which an alkoxide ion is a nucleophile that displaces a halide ion froman alkyl halide to give an ether.

Thus, here vinylic halide does not gives Williamson’s synthesis.
Therefore, $C H_{3} C H = C H - O - C H = C H_{2}$ ether cannot be prepared by direct Williamson’s synthesis.

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