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Question
Complete the following reaction sequence:
\[\ce{HC ≡ CH ->[LiNH2] A ->[CH3CH2Cl] B ->[HBr] C}\]
Comment on the acidic nature of B.
Solution
\[\ce{HC ≡ C - H ->[Li+NH2-][-NH3] \underset{(A)}{HC ≡ C -Li}}\]
\[\ce{HC ≡ C - Li + CH3CH2 - Cl ->[-LiCl] \underset{(But - 1 - yne)}{\underset{(B)}{HC ≡ C - CH2CH3}}}\]
\[\begin{array}{cc}
\ce{CH3 - CH2 - C ≡ CH + HBr -> CH3 - CH2 - C = CH2}\\
\phantom{.........................................}|\\
\phantom{.........................................}\ce{\underset{(2 - BromoBut - 1- ene)}{Br}}\\
\end{array}\]
Compound B is But - 1 - yne. It has acidic hydrogen as it is attached to sp hybridised carbon.
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