JEE Advanced 2010 Chemistry question

The synthesis of 3-octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an alkyne. The bromoalkane and alkyne respectively are

(A) and
(B) and
(C) and
(D) and Correct

Answer: (D)

Solution

Sodium amide removes the acidic terminal hydrogen of a 1-alkyne to give an acetylide ion, which then displaces bromide from a primary bromoalkane by : \mathrm{RC\equiv CH \xrightarrow{NaNH_2} RC\equiv C^-Na^+ \xrightarrow{R'Br} RC\equiv CR'}. 3-Octyne is , so the

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Question ID VK-025736