Addition of Amine Derivatives

Concept: Concept: Ammonia Derivatives

Video Transcript

In this video, we’re going to discuss all the different things that you can make when you react an ammonia derivative with a carbonyl.
At this point you should feel pretty comfortable with the reaction of ammonia with a carbonyl. We know that in the acidic environment, you add ammonia to a carbonyl and you're going to get it an imine, nitrogen double bond carbon. Looks like a carbonyl except it’s a nitrogen. What would happen if instead of reacting with NH3, you take out one of the Hs, so NH2 and you replace it with something else. Let's say you replace it with another amine. Then what would happen? This is where you get your imine derivatives. Ammonia derivatives are going to yield what we can call in general imine derivatives.
Because your imine derivatives all look exactly like imine except that they just have different functional groups coming off of the nitrogen. I would commit these to memory if I were you because they're functional groups you should know and you never know if your professor mixes it up and instead of giving you a normal amine gives you hydrazine.
Then what would happen? Hydrazine is the name of NH2 with another any NH2. When hydrazine reacts with a carbonyl in an acidic environment, it makes hydrazine. Damn, that's confusing. Hydrazine goes to hydrazone. It makes sense. The names are super similar but make sure that you don't mix up the two. One easy way to think about it is that hydrazine and ketone make hydrazone. Hydrazine would be the mixture of both. What if you reacted with an NH2 and an OH? That’s called a hydroxylamine and that's going to give you functional group called an oxime. An oxime would be an imine with an OH coming off of the top. Finally, if you were to take a hydrazine but put a phenol on it, that's a phenylhydrazine. Phenylhydrazine is going to yield phenylhydrazone when you react it with ketone.
These are all different combinations that all follow the exact same mechanism as an imine addition except that they're just derivatives of an amine that reacts to make a derivative of the imine as a product. Now, I’m giving you a problem down here. Go ahead and see what you get. See if you can figure out how to react this big molecule with ketone and then I'll show you the answer.