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19. Aldehydes and Ketones:Nucleophilic Addition

Cyanohydrin

19. Aldehydes and Ketones:Nucleophilic Addition

Cyanohydrin

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1

concept

Addition of Cyanide

3m

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Now that we understand the general mechanism of nuclear Filic edition, it's important to really understand the specific nuclear files that can attack carbon eels and make substituted alcohol's. One of the most famous of these is cyanide. So Cyanide is a negatively charged nuclear file that's used to make a functional group called the Scion. Oh, hydrant, you might already kind of be ableto Guess what? That is just by the name, But I'll show you So typically, CNN is reacted as a negatively charged and I am So I mean, N a C n is very common, but you could also see Casey N. This is very a very common way to represent it as well. And as you can imagine, guys, this is just straight up nuclear full condition. I've got my cnegative. I've got my very strong, partial, positive charge. So I get a nuclear feel like addition mechanism. What this is gonna make is a negatively charged oxide and my CNN so stitch want. Okay, so that is what I get after the first step. And then there's always gonna be a pro nation step that you can use. You could use water or some kind of mild acid tau protein e. Obviously, that's not the mechanism for prote nation would be something like this and like that, and you would get your functional group in your functional group whenever you have a CNN and an O. H on the same genital to each other. Okay, that's called a scion a hydrant. Okay, No, guys, I wanted to inform you that there's another form of CNN that's actually pretty common as well. That doesn't require protein Nation step. And that one I'm gonna race a few arrows. If you don't mind, You can keep the ones that you have on your page, but I want to show you guys another example would be if I used or if I used h c n. Okay, Now HCM is a really interesting compound because if you just look at it, you might think, Oh, that's a source of CIA negative. But remember that the carbon hydrogen bond is actually a very strong bond, and usually carbon and hydrogen doesn't just ionized like that. That's actually a co violent bond. Covalin bonds usually don't just disassociate to make H plus and see a negative. That's kind of strange why would it do such a thing? And the answer has to do with acidity. Guys. So it turns out that it's not that it's a weak bond in terms of polarity, that there's a die poll. But it turns out that there's a very acidic bond. Okay, it turns out that H c n if you guys remember your PKK's way back in the day has a PK of about 10. Okay, so in normal acquis environments, it's gonna be, um, ionized. It's gonna be an ionized form. Now, the advantage of using H c N is that Look what you've got. You've got the cnegative again. You've also got your proton to protein eat so you could do any CNN and then water. Or you could just do h c n and oh my gosh, that's not what I want to dio. Or you could just use H c N and H Scene will take care of both steps. Okay, it will do the nuclear feel like addition, and you'll go ahead and you'll add your hydrogen. Okay, so for the pro nation steps, So now what I want to do is I specifically want to talk about two other reactions that happen with Sino hydrants that really have nothing to do with the nuclear field edition. But as a functional group we should be aware of. What can you do to assign a hydrant? And now that's what we're gonna do in the next two videos. Let's go ahead and start off with the first Sino hygiene reaction.

2

concept

Nitrile Hydrolysis

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All right, So now that we know what a scion a hydrant is, let's go ahead and draw that in. We've got an O. H on one side and a C drill. One end on the other. Okay, well, the first thing you should be aware of is that I mean, we have a night trial, right? That's the name of the functional group of CNN is called a night trial. Altogether. This is called a Sino hydrogen. Well, it turns out that night trials are actually in a category of molecules called Khar Buck Cilic acid derivatives. And if this is something that you've already learned at this point, of course, then this is gonna make perfect sense. If not, that's fine. I'm just gonna help you guys understand it now. But it turns out that car oxalic acid derivatives are a category of molecule that by definition, can be hydrolyzed to carb oxalic acid. Okay. And I'll just draw it out. Okay, so it's in a category of molecule that can be hydrolyzed. Okay, there's a whole section of organic chemistry just dealing with carbolic acid derivatives. So obviously, if you want more information, go there. Okay. But right here. We're just gonna summarize it to say that you could There's acid and base catalyzed mechanisms for this to happen. So any combination of acid and water or base is going to get this toe hydrolyzed. Okay, so you can see here. I have water with acid with base, and he he can always help with these reactions. You can always hope to hide. Relies something. So what you're gonna get is nothing happens to the alcohol that stays the same. But we would just expect since is the carb oxalic acid derivative I'm gonna get Ah, carb oxalic acid here. Okay. So really, that's it, guys, this is not specific to Sino hydrants. It's specific just to night trials. So if you understand that night trial is a corpus LaGrassa derivative, then this reaction really isn't anything new. It's just a application off a karmic Selic acid derivative reaction. Okay, awesome guys. So that's it for that one. Let's move on to another

3

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Nitrile Reduction

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once again since we know what a Sino hydro is. Let's draw it. I've got my Ohh! I've got my Citro bond end. And what is Sino hydro reduction? Well again, guys, this has to do really with night trials, Not with Sino hydro owns. Okay, just that since you have a night trial present, night trials have the ability to be reduced. Okay. And night trials are very often reduced. Two primary amines. Okay, So if you want more information on this specific reaction, then you could go to the amine section of Arc Lush videos because there are going to discuss in much more depth the exact reducing agents that could be used for all types of, um, nitrogen derivatives that can be turned into a means. But for right now, since we're here anyway, let's just reinforce that There are a few very popular reducing agents that could be used to turn the C n compound into a primary amine the number one being lithium aluminum hydride. When in doubt, use LH that think for pretty much everything it blasts like pretty much all the double bond pi bonds. So lithium aluminum hydride works also just recognized these reagents. That's catalytic hydrogenation. So obviously doesn't have to be nickel. It could be palladium or platinum. And catalytic hydrogenation would also take out the triple bond. And what you get instead is nothing happens to the alcohol. It's actually very difficult to reduce an alcohol. Okay, um, but the CNN is very easy to reduce. So that's gonna become I'm gonna need to go off the screen a little or off the box a little bit. It's gonna be C H two and each to Okay, now, what's really important, guys is that you remember that this carbon exists. So don't just turn the CME group into a nitrogen. Well, that would be a big mistake. If you listen like this, you draw it a CNN, and then when you reduce it, you draw. It is N. H two. I've seen tons of students make that mistake. That's wrong. Okay, because if you're reducing CNN, you're actually reducing it to C. H two and h two, right, because there's a carbon and there's a nitrogen. Okay, so make sure to do that correctly, but other than that really easy reaction again, this really comes from your me in section of organic chemistry. I'm just reinforcing that here, since we're learning how to make a sign. A hydrant. Awesome. So let's move on to the next topic.

4

Problem

Problem

Provide the major product for the following reaction.

A

B

C

D

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