# Reaction of alkyne with sodium in ethanol

What is the product obtained on the reaction of but-2-yne with $\ce{Na}$ in ethanol?

I know that $\ce{Na}$ in liquid $\ce{NH3}$ converts an alkyne to an alkene by anti addition, and $\ce{Na}$ in ethanol is the principle reagent in Bouveault Blanc Reduction, but what about this reaction.

The answer given in my book is a trans-alkene. Is this a standard reaction? Also does it depend if it is a terminal alkyne or not? (I guess yes, because the terminal alkyne will try to deprotonate)

• Do you correctly decipher the question? The reduction by Na in liquid ammonia is followed by addition of ethanol as a source of protons. If you insist on your reaction process, addition of sodium metal into but-2-yne in ethanol will lead to formation of sodium ethanoate, which can add on the triple bond, leading to trans alkene. For further references see Houben-Weyl, books.google.de/… – ssavec Feb 16 '16 at 10:18