In the reaction H−C≡CH(1)NaNH2/liq.NH3−−−−−−−−−−−−→(2)CH3CH2BrX(1)NaNH2/liq.NH3−−−−−−−−−−−−→(2)CH3CH2BrY, Xand Y are:
A
X = 1 - Butyne; Y = 3 - Hexyne
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B
X = 2 - Butyne; Y = 3 - Hexyane
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C
X = 2 - Butyne; Y = 2 - Hexyane
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D
X = 1 - Butyne; Y = 2 - Hexyane
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Solution
The correct option is B X = 2 - Butyne; Y = 3 - Hexyane Higher alkynes are prepared from terminal alkynes like acetylene by treating it with sodium metal at high temperature or with sodamide(NaNH2). NaNH2 is a strong base which on reacting with terminal alkyne removes terminal acidic hydrogen leaving alkynyl carbanion, which on reaction with alkyl halide produces longer alkyne by nucleophilic substitution. Here NH−2 attacks the acetylene and removes the acidic proton and the carbanion formed attack the ethyl bromide to form 1-Butyne (higher alkyne). Again, excess NH−2 attacks the terminal alkyne of 1-Butyne to form carbanion and the process repeats to give 3-Hexyne. Thus, X is 1-Butyne and Y is 3-Hexyne.