Organometallics on Nitriles

Concept: Concept: General Reaction

Video Transcript

In this video, we're going to talk about how you can make ketones from nitriles. Like carbonyls, nitriles have a very strong dipole along the carbon nitrogen bond which is going to make the carbon highly electrophilic. This is very similar to carbonyls. That means that when you react a nitrile with a nucleophile, you can expect to get nucleophilic addition. Very popular nucleophiles that we've used in the section are organometallics like Grignard, RMgBr. and RLi. Remember that these reagents have full negative charges on them. What’s also advantageous about them is that they have alkyl group so that they can add Rs. It turns out that if you use one of these reagents on a nitrile in acidic environment, you’re going to get a ketone. The R group here is actually coming from the Grignard or the organolithium. That R gets added to the carbon and winds up turning into a carbonyl. You might be a little bit confused because you're thinking, “Johnny, what happened to the nitrogen?” We had a nitrogen. It really looks nothing like the original compound. For this, we’re going to have to go into the mechanism which yes, I'll show you the whole mechanism. But it turns out that this mechanism is going to make a lot more sense you than you think because it's really just a variation of stuff we’ve learned before. In this next video, I’m going to show you the full mechanism for how you can turn a nitrile into a ketone.