20. Carboxylic Acid Derivatives:NAS
Carboxylic Acid Derivatives
Carboxylic acid derivatives are defined as any carbonyl with a single electronegative group (–Z) in the α-position.
Intro to Carboxylic Acid Derivatives
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Hey, everyone, On this next page, we're gonna define two extremely important concepts that are gonna be essential for this next topic. Okay, the two things we're gonna define is what is a carb oxalic acid derivative? It's a category of molecule and the mechanism that it undergoes N A s or nuclear feel like a seal substitution. So let's start off with the first question. What is a carb oxalic acid derivative? Well, it's simply defined as any carbon eel that has an Electra negative z group in the Alfa position. Okay, so it's kind of a lot to chew on. Let's break that down, Okay? We'll remember that in ketones and alcohols hides, you're usually stuck. I mean, by definition you're stuck with an R Orrin h. Okay, now are an h r. Not electro negative at all. In fact, they make terrible leaving groups. If you think about H negative, that's a strong base, are negative. That's an even stronger base. These things are not good leaving groups okay, so we find is that there's a certain mechanism that they tend to undergo which we'll see in a second, whereas Z groups are defined as something that's slightly election, negative, even toe. Very election. Negative. So here are all the Z groups that we're gonna be working within this section. We've got chlorine. We've got, like, basically an Esther, Um, O R O H N h 20 k or Oh, that's the type of that should actually be NH two. Negative. So sorry about that. You could just fix that. Okay. Even tutors make mistakes sometimes. So, guys, So those are our Z groups now, notice that they're not all quite as good. Electra negative groups. Like, for example, chlorine is very Electra negative. Nitrogen? Not so much. But the reason that we cluster them all together is because, hey, they're much better than our groups in hydrogen. Okay, no matter what. Okay, So it turns out that by definition, these Z groups okay are gonna allow these carbon eels to follow a new mechanism That's different from the mechanism that we would see in the keystone alga hide called nes or nuclear filic. A seal substitution. Okay, now, a few more definitions about carb oxalic acid derivatives. Okay, by definition, anything that we call a carb oxalic acid derivative can be hydrolyzed back to carve oxalic acid using a combination of water with acid or base. So if I ever tell you that this is a carb oxalic acid derivative, that is me saying that you could use water. Tow hide relies it back to carve oxalic acid, which, as you see car oxalic acid, would be if I used an 08 Right? So, Carl oxalic acid is also a Z group is just It's a specific one. Okay, so carb oxalic acid you could think of as the mother of all of the other car looks like acid derivatives because you could always turn those derivatives back into car oxalic acid with hydraulics. ISS Okay, now, another really strange little fact here is that NYT trials also fall into this category due to their ability to be hydrolyzed. So we're going to see later guys that notice that I don't have night trial on my list, but night trials look like this. Okay? I'm looking for a place to write it. Carbon nitrogen like that. And it turns out that they could be hydrolyzed using basically water and acid or base to car books like acid. So we consider night trials. Toe also be car books, like acid derivatives. Okay, so in this next video, what I'm gonna do is I'm going to show you guys the differences between nuclear feel, like addition, which is the mechanism that ketones and alcohols undergo versus nuclear Filic Aysal substitution. Which is what carpet cilic acid derivatives undergo.
Intro to Nucleophilic Acyl Substituion
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Alright, guys. So even if you haven't studied your key tones and Alba hides chapter yet, you should still know about nuclear Filic Edition because there are even some reactions from organic chemistry one that had nuclear filic edition. Okay, so first we want to show you is what happens when a nuclear fault interacts with a key tone or in Alba hide. Well, what we get is that a nuclear file attacks the carbon. No, carbon. Why? Because it's highly, positively charged. You've got a strong die pull pulling away from that carbon. Now, if we make that bond, we have to break a bond. So we're gonna break upon up to the O And what we're gonna do is we're gonna get this very famous intermediate called a Tetra Hydro Intermediate. Okay, that Tetra Hydro Intermediate is now gonna have a new nuclear file attached to it. All right, whatever you wanted, whatever had the negative charge. Now this touch of federal intermediate is going to protein eat. The reason is because there's nothing else that it could do. Okay, If it was to try to reform a double bond, it would First of all, it would break the octet here if you tried to make a double bond again, but also, it would have no bond to break. Remember that if you make a bond, you could try to break upon to preserve the octet. But all of these leaving groups suck if you notice are, would make our negative if I try to break it. Okay. Is our negative a good leaving group, guys, it blows. It's the worst ever. Okay, how about the nuclear file? Well, guys, the nuclear falls, the thing that attacked, so obviously it's not gonna wanna come off now. That's what started the reaction. So anyway, this negative is stuck. It's gonna protein ate with some acid, and we get a substituted alcohol. Okay. And this is the mechanism that organic metallics undergo that all that most reducing agents undergo. So this should be somewhat familiar to you at this point. Okay, Now, let's look at some interesting changes that happen when you add a Z group. So, guys, the nuclear file, let's say we're just using the same exact nuclear file. The nuclear file is still gonna be attracted to the same exact carbon because it's still Electra Filic in fact, maybe even more so because notice that now we have a Z groups that Z Group could be even activating it Mawr towards attack. The difference is with the Tetrahedron intermediate guys, because what we're gonna get is a negative and a nuclear file. And this negative is different than the last one. Because the last one was stuck, there was nothing I could do, because if it tried to reform a double bond, it would violate an octet. It didn't have a good leaving group, but Z groups can leave. Depending on the environment, we can make the group's leave. So in this mechanism, instead of protein eating, your negative charge actually reforms the double bond and kicks out the Z group. Okay, so this asset acidified acidification step the pronation step doesn't happen because it's just going to reform the carbon eel. So we wind up getting is a double bond here, So draw that in. Guys, I want you to draw this in for yourself and you get the new nuclear file Now. Notice what just happened, guys, I started off with one substitue int on the carbon eel and I ended up with another I just did a substitution How it changed, Z for whatever my nuclear fall Waas. So instead of getting what we called a substituted alcohol at the top, we're gonna get a substituted carbon Neil, because you preserve the carbon, will you just change the our group? Okay, so this mechanism is called not nuclear Filic addition. It's called nuclear Filic Aysal substitution. This is the mechanism that all carb oxalic acid derivatives undergo. Okay? And it's gonna be the subject of an entire field of chemistry that has to do with car oxalic acid derivative chemistry. Okay, so these mechanisms start off the same, but they end up very different because of the presence of that Z group. All right, so let's move on.
Additional resources for Carboxylic Acid Derivatives
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