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Q.

Which among the following will give 3,3–dimethylbut–1–yne on reaction with  NaNH2/

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a

1,4–dibromo–3,3–dimethylbutane 

b

2,2–dibromo–3,3–dimethylbutane

c

1,2–dibromo–3,3–dimethylbutane 

d

Both (2) and (3) 

answer is D.

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Detailed Solution

1,2–dibromo–3,3–dimethylbutane undergo dehydrohalogenation reaction in the presence of NaNH2 in liquid NH3  and forms 3,3–dimethyl but–1–yne.

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2,2–dibromo–3,3–dimethylbutane undergo dehydrohalogenation reaction in the presence of NaNH2 in liquid NH3 and forms 3,3–dimethylbut–1–yne.

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