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Master Organic Chemistry Reaction Guide

Deprotonation of alkynes with base to give acetylide ions

Description: Treatment of an acetylene with a strong base such as NaNH2 results in acetylide ions

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Real-Life Example:

Org. Synth. 1962, 42, 97
DOI Link: 10.15227/orgsyn.042.0097

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8 thoughts on “Deprotonation of alkynes with base to give acetylide ions

  1. I’ve got an exam question problem: So I’ve added n-BuLi to an alkyne, from this a suspect I product lithium acetylide, however the question asks for ANOTHER reagent in the reaction, could it be LiH4-, to get rid of the lithium or is there something im missing?

    1. tBuCl is not a base; do you mean t-BuO(-) ? Given the large pKa difference between tBuoH (17) and alkyne (25) the equilibrium will lie on the side of t-BuO- , so it’s more useful to use a strong base like NaNH2 (pka of conjugate acid 38) to deprotonate the alkyne irreversibly.

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