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Reduction of 2-butyne with sodium in liquid ammonia gives predominantly

1. cis-2-butene
2. No reaction
3. trans-2-butene
4. n-butane

Correct answer: trans-2-butene

Solution

Reduction of alkynes with sodium in liquid ammonia follows a dissolving metal reduction mechanism, which selectively produces the trans-alkene due to the anti-addition of hydrogen atoms.

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