Which of the following reagents will be able to distinguish between 1-butyne and 2-butyne?
- NaNH2
- HCl
- O2
- Br2
Answer
(1) NaNH2
Solution
1-Butyne is a terminal alkyne; its C–H hydrogen is acidic (sp carbon). 2-Butyne has no hydrogen on a triple-bonded carbon.
CH3CH2C CH + NaNH2 CH3CH2C C-Na+ + NH3
CH3C CCH3 + NaNH2 no reaction
∴ Sodamide reacts with 1-butyne (liberating NH3) but not with 2-butyne, so it distinguishes them.
HCl and Br2 add to both triple bonds, and O2 burns both, so they cannot distinguish.
Answer: (1)