Nitriles present hydrogens to acids that can be removed with strong bases, forming nitrile enolates. These hydrogens have a pKa of 25.
![enolates-nitrile enolatos-nitrilo](/images/stories/organica-ii/nitrilos/enolatos/enolatos-ntirilo-01.png)
Nitrile enolates are resonance stabilized and are good nucleophiles, capable of attacking a wide variety of electrophiles.
![enolates-nitrile enolatos-nitrilo](/images/stories/organica-ii/nitrilos/enolatos/enolatos-ntirilo-02.png)