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  • Alkynes on reduction with sodium in liquid ammonia form trans alkenes. Will the butene thus formed on reduction of 2-butyne show the geometrical isomerism?

Alkynes on reduction with sodium in liquid ammonia form trans alkenes. Will the butene thus formed on reduction of 2-butyne show the geometrical isomerism?

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Butene-2, where either both the methyl groups are on the same side or opposite side to show geometrical isomers, is formed on the reduction of 2-Butyne.

H_{3}C-C\equiv C-CH_{3}\overset{Na/liq.NH_{3}}{\rightarrow}    

This reaction is called dissolving-metal reduction. When sodium is dissolved in liquid ammonia, it loses an electron to the solvent, creating a solvated electron. These solvated electrons are strong reducing agents that add to the alkyne triple bond.The reaction proceeds with an anti addition of hydrogen across the carbon–carbon triple bond. The trans configuration is favored because it minimizes electronic repulsions.

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