Alkylation using a ACETYLIDE ion.
Acidity of Terminal Alkynes
- Terminal alkynes are more acidic than alkenes and alkanes.
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.
- The base that removes the proton must be stronger than the base that is formed.
Alkylation using a Acetylide ion
- 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.
