Partial reduction of alkynes to trans alkenes using sodium and ammonia

by James

Description: Alkynes treated with sodium in ammonia are reduced to trans alkenes. Alternatively, potassium in ammonia can also be used.
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{ 2 comments… read them below or add one }

Seah October 24, 2013 at 7:03 am

Why is the radical anion able to undergo flipping when there is a pi bond? Does that require a great amount of energy to first break the pi bond, flip and then reform the pi bond again?

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Ryan McCauslin November 26, 2013 at 5:48 pm

I was wondering the same thing….? Prehaps the alkyne pi bond cleavage actually takes electrons from each of the separate pi bonds which allows temporary alkane rotation to form the more stable trans intermediate?

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