Acetylide ions: Alkylation

 
   
 

Terminal alkynes can be alkylated with primary alkyl halides

Mechanism

 
 
Terminal alkynes are deprotonated with the strong base to give an acetylide ion.
This acetylide ion will react with the alkyl halide by an SN2 mechanism. The acetylide ion is very basic and promotes elimination with secondary halides.