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Question

When vicinal dibromide is heated with KOH in ethanol followed by sodamide (200C), double dehydrohalogenation takes place giving alkyne. Which of the following fails to give alkyne according to this procedure?

A
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B
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C
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D
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Solution

The correct option is C
Vicinal dihalides on treatment with alcoholic KOH undergo dehydrohalogenation. One molecule of HX is eliminated to form alkenyl halide which on treatment with sodamide gives alkyne.
Triple bond can not be formed here in option (c) between the carbons bearing bromine atoms because if triple bond will be formed, the valency of carbon atom will not satisfied. All other compound give dehydrohalogenation to give alkyne.
Hence, the correct answer is option (c).

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