The reaction of an acetylide ion with an alkyl halide.
Alkylation using a Acetylide ion [7-11]
- One important reaction that forms a C–C bond is the reaction of an acetylide ion with an alkyl halide.
- Only primary alkyl halides or methyl halides should be used in this reaction.
Acidity of Terminal Alkynes [7-10]
The sp carbon of the acetylide anion is more stabilized due to the presence of a negative charge where the S orbital accounts for 50% of the charge.
- Terminal alkynes are more acidic than alkenes and alkanes.
- The base that removes the proton must be stronger than the base that is formed.
