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Question

Which one of the following do not give Birch reduction?

A
But-1-yne
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B
Hex-1-yne
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C
Hex-2-yne
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D
(a) and (b) above.
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Solution

The correct option is D (a) and (b) above.
Terminal alkyne does not show Birch reduction due to the acidic nature of terminal Hydrogen, it reacts with Na/liq.NH3 to liberate H2.
Since But-1-yne and Hex-1-yne are terminal alkyne hence they donot undergoes birch reduction.
CH3CH2CHCHNa/liqNH3CH3CH2CCNa++12H2
Hex-2-yne will undergoes birch reduction and gives trans alkene as a major product.

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