A functional group with the general formula R–C≡N. The simplest nitrile is acetonitrile, CH3CN. Nitriles are commonly made through nucleophilic substitution of alkyl halides with cyanide ion or through dehydration of amides with POCl3. The alpha-carbon of nitriles is weakly acidic (pKa ~ 30) and their enolates can be formed with strong base.