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Question

In the reaction HCCH(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 NH2 attacks the acetylene and removes the acidic proton and the carbanion formed attack the ethyl bromide to form 1-Butyne (higher alkyne).
Again, excess NH2 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.


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