Formation of alkynes through double elimination of vicinal dibromides

by James

Description: Sodium amide will convert 1,2-dihalides (“vicinal dihalides”) into alkynes through two consecutive elimination reactions.
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{ 4 comments… read them below or add one }

Quinn Haynie March 20, 2013 at 9:20 pm

My course taught us that we need three molar equivalents of NaNH2 for this reaction, as it prevents the formation of the alkynyl salt.

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james March 20, 2013 at 10:23 pm

True, for terminal alkynes. Once the alkyne is formed, it can then be deprotonated by NaNH2 in solution. For practical purposes, three equivalents for the formation of terminal alkynes is best.

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Jason Mathias March 6, 2014 at 3:39 pm

Does this work the same way for Geminal Dihalides?

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James March 9, 2014 at 8:49 pm

Yes it does!

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