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Question

A compound on dehydrohalogenation with alcoholic KOH gives alkyne but on dehalogenation with zinc dust gives alkene. The compound is:

A
C2H5Br
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B
CH3CHBr2
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C
CH2BrCH2Br
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D
CHBr2CHBr2
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Solution

The correct option is C CH2BrCH2Br
Reaction with Zn
CH2BrCH2Br+ZnCH2=CH2+ZnBr2
Reaction with alc. KOH
BrH2CCH2BrAlcoholicKOH−−−−−−−−1,2dibromo ethane(vicdihalide)
H2C=CHBrNaNH2−−−−CHCH+NaBr+NH3

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