Organic Chemistry

Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.

23. Amines

Nitrogenous Nucleophiles



Four Ways to Make a Primary Amine Precursor

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Hey, guys, if you've watched my A means by reduction video already, then you'll know how important reduction reactions are to making primary means. If you haven't watched already, you need to go back and watch it because the concepts in this video are gonna build upon the cheat sheet that I taught you in that one. Well, in this video we're going to discuss is how you don't always have to start with those highly oxidized nitrogen compounds to get to a primary mean. Sometimes you can start off with just a alcohol. Hey, lied and use nitrogen in an S and two reaction to get to a primary Amine eventually. So let's check this out. So three of the re agents that were the starting compounds in my A means by reduction video can be found as excellent nuclear files. So it turns out that some of the ways that we can make those oxidized nitrogen compounds is to use nitrogen as a nuclear fall first in an S and two reactions. So that's we're gonna right here. They're gonna participate in S and two reactions because it works. If there's a good leaving group present. Okay, Now, obviously. Maybe it's been a while since s in two, so I need to brush up a little bit, but it's really easy. It's backside attack. Right? So let me just show you guys an example of what I'm talking about. And then maybe you'll understand what I'm saying. Here I have a secondary alcohol. Hey, light right on. What we learned back with s and two is, that s And two is favorite for secondary alcohol highlights. If you have a strong nuclear file, you have a good nuclear awesome. That's good at donating electrons. Well, a really easy way to put a nitrogen. Where that ronin is is to react it, for example, with see and negative. Remember, seat and negative is a strong nuclear file that we used plenty in organic chemistry. One, this would do a backside attack. It would attack the backside. It would kick out the bro. Mean, And what would you get as a consequence? Well, we would get a product that now looks like this. See, Triple bond end. Okay, now that we have a night trial, how could I turn this into a primary mean? Do you remember any re agents that would work on this to make it into a carbon with an N H. Two and by guys. I'm sorry I went off the screen there, so I'll put the age of the bottom to Perfect. Okay, So what re agents could be used to turn a CN group into a primary mean, guys, this is our common reducing agents. Okay, So I'm trying to do is I'm trying to take you a step backwards, and I'm trying to say, if you don't have a night trial already what Regent? What nuclear file could we use to get there? Okay, so now I'm gonna show you some other ones, so CNN is a possibility. Can you think of any others? How about and so too negative? No, to negative is a strong nuclear followed we've used before. It can also do a backside attack, and we would get a nitro group. So how can we reduce Nitro guys into Inamine? What regions could we use for that again? We can use our common reducing agents. Do you remember? Maybe a more chemo selective reduction That's Onley gonna work on the n one case You did it or Maybe you did. It's your Stannis chloride, right? So it's gonna be your tin to chloride. Your tin to chloride is your chemo selective version. That's just gonna pick the n 02 mighty. And it's just gonna reduce that. Awesome. So what's another nuclear fall? Rack your brain here? Think. What's another of those six reduced reduction reactions? What's another one that we could make through an S and two reaction? Well, maybe you thought about it already. We could make an aside. Okay, Because n three negative is a strong nuclear file. So we could do a backside attack with that Would give us is a compound that looks like this N three. Okay, now, what re agents could we use on end three to turn it into a primary amine? And the answer, guys, this one's a little bit weird. We can't use the common reducing agents. We would have to use your try. Fennel foss fiend and water. Okay, So the point of this whole lesson here is that I want to show you that you don't always need to start off at thes middle steps. You don't always have to start off with an aside. you can create an aside through essence you by using the nuclear feel like properties of those nitrogen. Okay, now, on top of that, there's one more that we can't make through an S and two. But we can still make it through a negatively charged species. And that is and three and three negative. Remember that and three negative can do a substitution reaction with in acid chloride, right? And this isn't the full mechanism, but this is like the abridged mechanism. The full mechanism is called nuclear feel like a seal substitution. So that one you can look up on your own. You can type in nuclear feel like a cell substitution into the clutch search bar, and you'll find a whole video on that and what we find. So I have here n three negative can act on acid chlorate, produce a seal asides. And like I said, it's not, in essence, you mechanism, but we talked about it in another video. It's an n a s mechanism, and what you wind up getting is is your aside. Do you guys remember how you can turn in a sealed aside into? And I mean, this would look like this. What regions could use for that? Well, guys, this one would be the courteous rearrangement and the regions for courteous were just heat and water. Okay, so just showing you guys how you don't always have to start off with that highly oxidized nitrogen. You can add the nitrogen because nitrogen is in a lot of nuclear full of compounds. Okay, so I want to do next, is just go ahead and do this practice problem and see how far you can get. Now, I will warn you guys that the third re agent, I'm just gonna tell you right now this is a reaction called a dyas on ization dyas on a die as on ization. And you might not know it yet, depending on if you've watched this video or not. So if you don't know the last one no hurt feelings. Just go ahead and watch me solve it. But at least you should be able to do the first two okay. And then I'll go ahead and finish up the last part for you guys. So go ahead and do it


Provide the Major Product

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Alright, guys. So the first step here would just be an s into a ness and two mechanism because we know that end three is going to do a backside attack. So what I would get for the first step is now end three, and that's your first step. So now we're second step pH three p N h 20 This is our try fennel philosophy and reducing agent, and this is going to give me in a mean Okay, So now I have ah, primary mean because I start off with an alcohol. Hey, Light that could do in s and two. Now, The last step, which you may or may not have known, is, uh adds a die as a group. So what this does is it's going to turn my NH two into and triple bunt and positive. Okay? It makes what's called a die as a group. Okay, Now, this is important because dyas or reactions are one of the more common applications of a means we can turn. It means directly into dyas. Oh, um, using n 02 uh, negative and hcl. Okay, but in case you didn't know that if you haven't gotten to that video yet? It's not a big deal. Okay, Awesome, guys. So I hope that I was able to make my point here, that you can actually make most of the nitrogen starting compounds that you need to get to where you want to go, which is eventually to make that primary. I mean, awesome. So let's just keep moving on.