in this next page, we're gonna talk about the nuclear Filic edition off neutral a means to carbon eels. And this is going to yield it means and any means. Alright, guys. So the difference between an Emmy in and Inamine is simply gonna be the type of a mean that the carbon eel is reacting with. Okay, as you guys can see when you erect a carbon deal with a primary amine Okay, you're going to get an A mean in a mean has a functional group of basically a nitrogen with a double bond on it and possibly in our group on the top. Okay, so think about an M Mean is kind of like a carbon, Neil. Oh, wow. Carving Lee carbon meal, but with the nitrogen. Okay, so if you can think about if you if it would have been a carbon deal with an oxygen that's an Emmy with a nitrogen on it. Now notice that when I react a secondary amine, I get a different looking compound. Now, this moment has to our groups, and instead of getting the double bond directly on the end, I actually get it down towards one of the are groups. Now, we're gonna go through both of these mechanisms completely. But I just wanna ask you guys, why do you think that double bond might move? Why do you think it might be towards the bottom guys? Because if you have to our groups on your end, that means that if I were to put the double bond on the end, I would get a formal charge. Right. So to eliminate the formal charge, I'm gonna have to move the double bond down toe one of our groups. Okay? And that's the biggest difference between an I mean and an enemy in in fact, they're pretty much the same exact reaction, except for the final step. Okay, so what we're gonna do is we're gonna go through both of these mechanisms, and I do want to say one thing really quick that both of these mechanisms are gonna pass through Very important intermediate on that intermediate is called the mini, um, cat eye on the A mini. Um, Catalan looks like this. It's your nitrogen with a double bond and with two things on it. So either h is or ours and a plus charge. So two of these an A plus charge. Okay, so we're always gonna pass through the A mini, um, Cat ion. And then how we resolve that Cat Ion is what determines whether it's gonna be an Emmy in or an enemy. Okay, so let's go ahead and look into the mechanism of an Indian.
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Alright, guys. So when Imean is created, when a carbon meal reacts with a primary amine and acid. Okay. Now you can also use ammonia. Ammonia would be considered a zero degree. I mean, it's the same thing, So either zero degree or primary would both make an Emmy. Okay, Now you need an asset. So I'm gonna put H plus here. Okay. Now, for the purposes of this mechanism, I personally like if I combine my proton with my solvent so that I don't have multiple things or multiple types of regions I'm tryingto work with. So can you guys just go ahead and assume with me that age three plus each plus would give me n h four plus, and that's what I'm actually gonna react with. So for all of my reactions for both of these mechanisms, I'm just gonna use NH four plus, which is fine. You can use any acid you want whatever acid you, professor or your textbook gives you. Okay, so I'm gonna go ahead and draw it like this and h three each positive. What do you think is the first step of this acid catalyzed mechanism? You got it. Proto nation How did you guess? How did you guess? So now I'm gonna use reversible arrows, right? Not forwards arrows, and I'm gonna draw that. I have a double bond H carbon. This is a positive charge, and I'm gonna go ahead and draw resonant structure. I'm gonna draw this structure so that it can understand what this positive charges doing. Okay, now, just, you know, disclaimer. Your professor may not draw this residence structure, and that's okay, Okay, because it's still valid. Okay, So what I'm trying to say here is that there may be minor, different differences between my mechanism on the one that you learned in class. But again, this is a valid mechanism. And if you want to throw in a resident structure, it's totally fine. It's not. Your professor isn't gonna dock you for doing this, because this all the arrows, they're going to the same place eventually. Okay? Now what this is going to do, since I have a positive charges that's gonna yield a nuclear feel like attack. So let's go ahead and take our NH three has a lone pair, right? So it's very attracted to that positive charge. We're gonna do a nuclear feel like attack. And what we're going to get is a compound that looks like this we're gonna get Ohh. Um, well, are are so those just our groups and then n h three positive. Okay, let's look familiar at all. If you guys have gone through the asset, tell Henry has a talent as total mechanism. Pretty much everything has been the same up into this point. Okay, Now, the difference is gonna happen here. We're going to consolidate a few steps instead of deep protein ating this thing. We're just gonna go ahead and start trying to get rid of that alcohol so that we could do that is through a pro proton exchange. Okay, so one way that we a better way to right this NH three Positive. I know you have an eraser. Would be to take the three, change it to a to and then draw one h out. Okay, that's gonna allow me to do a proton exchange. So let me just write this down. We're doing this and this and this is going to yield a compound that now looks like this. Oh, h two positive. Um, and H two are are Okay, so let me go ahead and backtrack and write down all the steps. So we said that this first one was Protein Nation. The next one was nuclear Filic attack. Now we just got proton transfer, and now we're about to kick out the leaving group. Okay, But instead of it just leaving, we could actually use the electrons from my nitrogen to kick it out. What I could do is I could do make a double bond and kick out the water. Now, this is gonna make is a double bond end. Now, I just realize that my nitrogen is out the bottom. I kind of wanted to face it up. So if you guys don't mind, I'm gonna flip this molecule. I'm gonna flip it so that now, my end h two is at the top. Don't kill me. And it was making a double bond. So I'm gonna draw the told one facing down. And there's two are groups we're gonna put the are groups facing down positive charge. You guys recognize this Intermediate? This is the domini, um, cat ion. Okay. Plus, we would also get water leaving, right? Cool. Awesome. So now that is my compound. That's my mini, um, cat eye on. How do you think we can get rid of one of those? H is we can use the con. You get based. Remember? I had NH three hanging around, so I'm gonna use NH three and I got a d protein eat. I'm gonna take away an age, give the electrons to the end and what I'm going to get is my a mean, plus my catalytic acid. And plus, yeah, we did make a water, so we lost a water like that. Okay, so now my product is an m mean notice that how do I know this is an m mean? Because it looks like a carbon eel, except as of nitrogen in it. Does that make sense? Cool, guys. So I hope that it is a lot of steps, but if you've watched the Khenyeza teller or a subtle mechanism, this is extremely similar. If you haven't watched those mechanisms yet, then when you get to them, it will seem very similar to this. So I'm just trying toe show you guys how the mechanisms are very, very related. Okay. Oh, also, I think I messed up on an arrow up here. This is supposed to be reversible. Sorry about that. Get too excited with these mechanisms, but you have to make sure go back. If you make mistakes, it's always change it before you submit your exam. Right? Cool. So we're done with this one. Let's move on to any means.
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Alright, guys. So any means air created when a carbon Neil, we're just gonna take our simple key tone again. This is acetone reacts with a secondary amine in the presence of acids gonna put acid. And now it turns out guys that ah, lot of the secondary means that are used for the enemy in process are actually cyclic. Because if you put an end and ring, it's a secondary, right? So let's use a cyclic secondary mean, these were very, very common in organic chemistry. Okay, so a cyclic secondary. I mean, it could have not been, but I'm just using it just because okay, also, if you guys don't mind, let's go ahead and assume that my cyclic, I mean, plus, my proton is going to make the cons you get acid, which looks like this. Okay. Oh, wait. Which looks like it's two inches cool. So in my first step, I'm going to take my protein ated version or my acidic version of Miami. I'm gonna protein eat. What this is going to give me is of positively charged oxygen which, after you draw the resonance structure, will have ah, highly Electra Filic carbon. What happens now you got it. Nuclear Feel like attack. So I got my nitrogen My square I'm going to attack now if you guys don't mind so that I don't have so that we can avoid what happened last time I'm gonna draw the nitrogen facing up So I'm gonna draw that I have my nitrogen with my square, right, And that's attached two carbons and then at the bottom, I have my Ohh! Okay, on top of that, this nitrogen still has an h. So there's a positive charge. Okay, now, this is the part that we did our proton transfer. So now we do see everything is the same guys were doing Proton transfer. My oh is going to grab the h give its electrons to the end. I'm gonna get a molecule. Looks like this with my oh h two leaving group. And now, guys, I'm in the perfect position to make my mini, um, cat ion because I can take the lone pair from the end, make a double bond and kick out my water. That's actually an elimination reaction. So now that I do that, what I'm going to get is my mini, um cat ion my mini, um, Catalan Looks like this. Okay, so notice that now. By doing that, my mini, um, Catalan has a positive charge. Okay, so how do you think we can get rid of that? Positive charges go right here in mini. Um, Catalan. So how can we get rid of that positive charge? Well, for an a mean I could just deep protein ate it, and then that was it. Can I d protein ate this nitrogen. Guys, this nitrogen has no hydrogen is on it. So how do I get rid of that positive charge? Well, actually, the only way to get rid of the positive charge is to get rid of the double bond. So this is where your elimination or your depot nation reaction actually turns into an elimination reaction. What we're gonna do is, instead of deep rotating the end, we're gonna deep protein 81 of the H is next to the carbon. Kneel next to the old Carbondale. This is also called an alfa position, because the position next to the carbon he'll see this would have been the Alfa position of a carbon, Neil. So we're gonna basically take away in Alfa hydrogen. That's gonna be very important when we talk about reactions at the Alfa hydrogen for carbon deals, that's a huge Alfa. Carbon reactions are a huge part of organic chemistry. Okay, it's not got my mini, um, cat ion. What can I do? Protein ate it with with my neutral. I mean, so I'm gonna take my neutral mean I'm going to take away the h I'm gonna make a double bond and kick these electrons back up to the end, making my Inamine on my final Inamine Looks like this nitrogen with a double bomb here. Plus, I get my catalytic acid and I got a water again. Right That left. Okay, so let's go ahead and write down all the steps, because I know that I didn't do that in this one. So first we had Protein Nation. Then we had nuclear feel like attack. Okay, then we had proton exchange or proton transfer. Then this is what we call elimination that his elimination. Okay, that's an elimination reaction. And then this was deep protein nation cool guys. So now we have our Inamine. Now I do want to point something out, guys, which is that notice that this double bond here, I drew it to the right. But I could have also drawn it to the left, right? Like why did I drop the left just because I decided not to? They're both the same. But if you were tohave an asymmetrical ketone originally, then that means you have two possible enemies that could occur. You could have an enemy with the dull bon to the right and an enemy with the dull bon to the left. And if you have an asymmetrical key tone that you're starting with, you should be You will be responsible to draw both of those enemies on your exam because they could both happen. Right? Awesome. Okay, guys. So that's it for this mechanism. It looks terrible, but it wasn't so bad. Let's move on to the next topic.