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A metal acetylide is an alkyne for which the terminal proton (hydrogen) has been replaced by a metal such as sodium or an organolithium. So, for example, the alkyne CH3C≡CH could be deprotonated to form the acetylide ion CH3C≡C−. Once it has been deprotonated it becomes a strong nucleophile. Some acetylides, eg. silver acetylide or copper acetylide, are explosives.
Additional recommended knowledge
Acetylide ions are very useful in organic chemistry reactions in combining carbon chains, particularly addition and substitution reactions. One type of reaction displayed by acetylides are addition reactions with ketones to form tertiary alcohols. In the reaction in scheme 1 the alkyne proton of ethyl propiolate is deprotonated by n-butyllithium at -78°C to form lithium ethyl propiolate to which cyclopentanone is added forming a lithium alkoxide. Acetic acid is added to remove lithium and liberate the free alcohol.
Several modifications of the reaction with carbonyls are known:
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Metal_acetylide". A list of authors is available in Wikipedia.|