Now it’s time to introduce some of the most important nucleophiles in all of organic chemistry, alkynides.
Understanding how to convert terminal alkynes to alkynides.
Recall that most hydrocarbons are terrible acids, having pKas from 40-50. However, terminal alkynes (alkynes with a hydrogen) are uniquely acidic due to the hybridization effect, having a pKa of 25.
This means they can be easily deprotonated using a strong base (typically NaH or NaNH2).
The resulting conjugate base is known as a sodium alkynide, and these are often used to lengthen carbon chains to through SN2 reactions.
- For now, this will be the only way to increase the number of carbons in your product.
Let's take a look at the mechanism of akynide synthesis.
The mechanism of akynide synthesis.
Beware: You can only use this reaction with primary alkyl halides. Secondary alkyl halides will favor E2!
Let's put it all together!
Using double dehydrohalogenation to perform alkynide synthesis.
Predict the final product of the following reaction sequence.
- What is the major product of the reaction of 1 mol of propyne with each of the following reagents? j. the pro...
- What is the major product of the reaction of 1 mol of propyne with each of the following reagents? i. sodium ...
- Show how you might synthesize the following compounds, using acetylene and any suitable alkyl halides as your...
- b. Give two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to syn...
- What is the product of the reaction of an ester with excess acetylide ion followed by the addition of pyridini...
- b. Explain why ethyne should be alkylated before, rather than after, nucleophilic addition.