Organic Chemistry

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19. Aldehydes and Ketones:Nucleophilic Addition

Acid Chloride to Ketone



Ketones from acid chlorides

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Now we're gonna talk about the way that you could make key tones from acid chlorides. So acid chlorides and Esther's have something in common. They both have a pretty good leaving group next to the carbon eel. So if nuclear feel like addition takes place on that Carbonell Carbon, that leaving group is prompted toe leave, allowing a double bond to be reformed. Okay, this process is called nuclear feel like a seal substitution, and it's It's the subject of another set of videos. Okay, that could be found in your car books Look, acid derivatives chapter. But for right now, I'm trying to say Is that acid chlorides and Esther's? When reacted with Organa, metallics are going to react twice instead of reacting once. Let's take a look. First of all, we remember that organo metallics have a negative charge on the Are the M Ionized is we don't really care about it. The negative winds up attacking the carbon. We form a tetrahedron Intermediate. This makes a compound look like this. We've got our at the bottom. We've got our one. We've got o R. And what takes place next is that instead of protein ating, my own getting an alcohol. I wind up kicking out my O R group instead. Right. This This gives me a key tone for the time being. Okay? And this is the first step of a typical reaction of organo metallics with acid chlorides and Esther's. At first, it seems like you're going to get a key tone, and this video is about making key tone. So you're thinking awesome. I just got a key tone. Okay, again, this mechanism that we just discussed here is called nuclear Filic a seal substitution or N A s, and we're not gonna go into it too deeply. Just acknowledge that that's what's happening here. Okay, Now the problem is that the organo metallic is going to continue to react with this re agent because it's still got a carbon deal. Right? So we bring this molecule down and I forgot that wasn't r one and r and we tend to react with the green eared or the organo metallic twice. So I'm gonna then get another mechanism. Another nuclear filic attack. This time giving me a tetrahedron intermediate are are one are now notice that this our group that I started with that is on my organo metallic has now added twice right, because I did two separate mechanism with it. And now at this point, we don't have anything good to kick out. So typically this is pro nated, so we don't have a protein ating agent here. But remember that at the end of our gente metallics, we usually have some kind of protein ating agent, We'll just use H A for right now and we get what we call a di substituted alcohol. Now I'm calling it die substitute because I don't know if I started off with an argue or not. But what I do know is that I added the same our group twice. Okay, this is the way that organo metallics are usedto working on acid, chlorides and esters. And it presents a problem when you're trying to make key tones because we're not going to stop in the middle, right? We never stop here. We actually go through and make the alcohol. That's why here I said that they react twice. Yielding di substituted alcohol's. Okay, so how can we prevent this from happening? Well, it's actually pretty easy, guys, if we really are bent on making my ass a cord into a key tone. We can use a Gilman re Asian. Okay. Gilman region is also called a die alcohol. Cooperate. Okay, so you see to alcohol groups and a copper group. Um, what this looks like is literally a copper with two R's coming off of it now, lithium diet alcohol cooperates tends to be weaker than other organo metallics. So what's gonna happen is that they're going to stop after the first nuclear filic addition. In this case again, it's an N s reaction. It's gonna kick out the C L. But what you're gonna wind up getting is simply one reaction not twice not to. So you're gonna yield a key tone from your acid chloride. So just thio make this mechanism really straightforward. You've once again got your our group. Your are negative. It attacks you kick up the electrons, you got your own negative. Your cl your are. Then you kick out your C l. But then you stop there. You don't generate another equivalent of ar minus. Okay, This second equivalent does not occur because my organo metallic is weaker. I'm sorry I'm in the screen, but because my we're gonna Metallica's weaker. Ah, Gilman region is not going to react with the key tone. All right, so just keep in mind that if you use any other organo metallic, you're gonna go to alcohol because you're gonna act twice. But if you specifically use a Gilman Regent, you're gonna stop it. The key tone, which is what we want for this section. Awesome. So let's move on to the next video.

Provide the major product for the following reaction