Carboxylic Acid to Acid Chloride - Video Tutorials & Practice Problems
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Carboxylic acids can be converted into several carboxylic acid derivatives using specific reagents. These include acid chlorides, amides, and (indirectly) nitriles.
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Synthesis of Acid Chlorides
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Hey, guys. So on this page we're gonna focus on those specific Z type reactions that turned carve oxalic acid into other types of derivatives. And we're gonna go a little bit more in depth on specific re agents that can transform certain types of derivatives to each other. So the first one is the synthesis of acid chloride. Now, this should be difficult to do, because if you remember, acid chloride is the most reactive Aysal compound. It's all the way over here, right? So to get carb, oxalic acid all the way over here, I'm gonna need a strong re agent. And that's exactly what we're gonna use. Guys, you guys should have probably seen this reaction already at some point in organic chemistry. But the most, you know, the most common re Asian to do this is S O C. 02 Okay, that's a very common regent to add chlorine to all kinds of things to alcohols and two car bookseller gasses. But there are other regions we can use. We can also use that's supposed to be or we can also use PCL fought PCL three or PCL. Five thes re agents are full of chlorine, and they're particularly good at turning a carb oxalic acid into an acid chloride. Now this is helpful for us synthetically guys, because once you have an acid chloride, you could turn that into any other derivative because of how reactive it is in very high yield. Right? Awesome. So let's move on to the synthesis of Ammon's.
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Synthesis of Amides
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Alright, guys. So according to my three rules, would it be favorable to turn a car oxalic acid in tow? Amit, does that go in the right direction in terms of favorability? Remember that car looks like as it was in the middle of the page. And am it was all the way on the left side. Yes, it would be because car oxalic acid is more reactive than amad. And that's exactly what we see. Guys, when you react to carve oxalic acid with ammonia, you are going to get some amad. Okay, but there is a problem. It turns out that the energy difference between these two, um a so compounds isn't high enough to give us good yields of AM EDS and actually what winds up forming predominantly is an ammonium salt. Okay, now, the way around that is to use a lot of heat. When you're doing this reaction, if you use a lot of heat, you can dehydrate the salt back to an am it. Okay, so this reaction actually does follow the three rules. You know, you're thinking Well, why are you teaching you this? If we already learned it on the three rules Well, because it turns out that your yield is just a little bit too low to make it a great way to synthesize Um and, um, it okay, you have to use heat in order to force it toe to make the amad. Now, it turns out, in order to avoid those harsh heat conditions, um, chemists have found another molecule That's a dehydration agents. Okay, so is a D hydration agent, and this molecule is called D C C. Okay, so here I've shown you what the structure is. You might not need to know what the structure is, but you should know that D c c on this are the same thing. Okay. D C c when coupled with NH three dehydrates the amad by itself. We don't need heat, so it greatly increases our yield. So instead of having to use a lot of heat to get amad, we can combine energy three with D. C. C. And we're gonna get a huge yield of our amad so many times, you're going to see this Agent DCC used to boost thes reactions that are already favorable, but to make them happen in higher yield. Okay, so the whole point of this area is that you will understand what the role of D. C. C is. All right, so let's move on to the next one.
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Dehydration of Amides
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we've been talking this whole time about home night trials are car box LaGrassa, derivatives. But not once have I mentioned how to actually make a night trial, and it turns out that they're not that easy to make. There's actually only one re agent that we're really gonna learn in this course that helps us or one type of reaction. That's a dehydration reaction. So it turns out that really, the major way to make night trials in this course is going to be to dehydrate Hamed's. Okay, Now, this is a mechanism that I'm not gonna teach you and that you're most likely not responsible for. I've never seen it on an exam. Okay, you should just know the relations for it. We're gonna use either p 205 which is also seen sometimes as p 40 10 should be a dime er of that compound. So I'm just saying this is the same thing. Or you can use eso seal to both of these re agents are gonna dehydrate the amad and turn it into a night trial. Why is that important? Because this is the only way to make a night trial up until this point, we've never learned another way to do it, and this helps to bring it into the family of carbolic acid derivatives. Now, if I want to make a night trial, I know I have to make the amet first. And then I dehydrate the Amon. Alright, so let's move on to our last reaction.
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Hydrolysis of Nitriles
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Finally, we know that by definition, night trials can be hydrolyzed to Carl oxalic acid, and this happens both in base and an acid. But typically, it's an acid catalyzed reaction. Okay, so as you can imagine, um, you wind up getting water, attacking the carbon, Neil, you end up kicking electrons up to the end. I'm not going to show you guys the whole mechanism here, and it's not a mechanism that is highly emphasized in this section, but you can imagine that what you wind up getting is something that has, like, a night, and it's like an Indian derivative. Okay, you're gonna end up with something that looks something like this, right? And from there, we have an acid work up, right? So since we're already in an acidic environment, it's not hard to imagine how, through an acid work up. This Imean derivative could be turned into a car. Looks like acid. Okay, so that's really all I want to mention. I'm much more interested for you to just memorized these re agents and not specifically no, they're mechanisms since these air not very important mechanisms for this section of the course. Okay, so let's move on to the next page.