Arteleo Chemistry Journal

Acidity of terminal alkynes

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Terminal alkynes are acidic, and the end hydrogen can be removed as a proton by strong bases (e.g. organolithiums, Grignard reagents and NaNH2) to form metal acetylides and alkynides. They are strong nucleophiles and bases, and are protonated in the presence of water and acids. Therefore, metal acetylides and alkynides must be protected from water and acids.

Terminal alkyne

Lithium acetylide

CH3CH2MgBr

NaNH,

Alkynyl Grignard reagent

Sodium acetylide