When two equivalents of halide are present, bases can eliminate twice, creating alkynes as products
There are two types of dihalides that can create alkynes. These are described by the position wordsvicinal and geminal.
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concept
General features of double dehydrohalogenation.
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Now I want to talk about the way that we can use elimination to make all kinds instead of Al Keane's. So actually making triple bonds out of elimination. And it turns out that all we have to do in this case is do a D hydrogenation twice. So this is gonna be called is double D Hydrology Nation. So let's go ahead and figure out how this works. Basically, when we react, either when we are some kind of diet Hey, lied with two equivalent to the base, it's gonna be able to react twice, making an AL kind instead of an AL Keen. Okay, now there's actually two different ways that we can make die. Hey, Lights. And we haven't talked a whole lot about die. Hey, lives yet. So I'm gonna introduce them here. There's actually two different, very common types of daylight. There's visceral day. He leads, and there's Germinal Die highlights. Now these words visceral and germinal aren't unique to die highlights. They're actually just position words that we use in organic chemistry, just like we use the term terminal and internal stuff like that. These are words that just identify the locations of substantial ints so visceral. You may have already heard it, but visceral just means that they're next to each other. So visceral is basically a 12 relationship. Okay. And the way that I like to remember it, if you are struggling to remember what visceral I mean, there's this word called There's like, Oh, you're in the vicinity. Okay. Vicinity means that you're close by. And basically, that's what Visceral is that they're close to each other. They're not exactly in the same place, but they're in the vicinity of each other. They're in a one to relationship with each other. All right, then we have another word. Genital. Genital is another position word. In this case, it means that you have a 11 relationship. Okay, so that means that you're literally on the same carbon. So genital. The way I like to think of it is that genital sounds like Gemini and Gemini means twins. So you could think that these both things, whatever they are, whether Germinal Dial's germinal intelligence, um, that they're both coming off the same carbon. Okay. Regardless, both of these different types of die Hey, lines. Whether you're talking about that, they're next to each other or whether you're talking about that. They're on the same carbon. Both of them are going to be open to this type of attack a a type of attack called double D Hydrology Nation.
Let's take a look at the double dehydrohalogenation mechanism.
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example
The double dehydrohalogenation mechanism.
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Let's go ahead and see how that works. Basically, we would do is I'm gonna do the first one is a worked example. Then you guys will do the second one on your own. So first of all, let's go ahead and identify. Do we have a die? Hey, lied. Yes. What type is it? This would be a visceral detail. I'd cool. So I have a visceral day. He lied. And now I have to Equivalents of base. Okay, now that I have to equivalents of face, what that means is that this is going to favor the formation of an AL kind, not just to do whatever other types of reaction. There's actually a favor doing a double D hydrology nation. So what the mechanism look like? Well, it would just basically be an e two mechanism twice. So let's go ahead and identify our beta hydrogen. If this is my chlorine in the beta hydrogen I would use for this one would be the h down here because I need the hydrogen. That's beta to the Alfa Carbon in the Alfa would be right there. This is my beta for the red chlorine. If I want to eliminate this one. I'm gonna have to use a hydrogen. That's also Beta Thio it. So this would be the Alfa for that chlorine. This would be the beta so that I would use Ah, hydrogen over here. Okay? And that's the basic. That's basically the way it would work. So you would start off with your first equivalent. Okay? And we would just go ahead and eliminate one of these beta hydrogen. So let's go ahead and eliminate this blue in first, make a double bond and kick out the CL. Okay, so now what that's gonna make as a as a middle step is that's going to make a molecule that looks like this. Okay, so now I have a double bond and I have a chlorine present. Now, just so you know, this is the product that you get after one equivalent of base. Okay? And if you were asked to provide the products for just one equivalent, this could be one of the products. Okay, so just you know, this would be like halfway, but we know that we can perform another elimination now. Why? Because remember that this red hydrogen is still over here and this chlorine is still here. So we still have a beta hydrogen and a chlorine that could be eliminated. So now this is where my second equivalent comes in. I would use my second equivalent of base, and I will do this again, make a triple bond and kick out the CL. What this is now going to create is simply a cyclo plantain with a triple bond coming off of it. And that's it. And then plus, we would have my two equivalent of ethanol and would have my to leaving groups. Okay, so that would be what we would get there. Now, some of you guys might be wondering, um, does this trouble one have Ah, hydrogen on it. Yes, it does. There's a hydrogen right there. I'm writing it in black. That's why black hydrogen, Where did that hydrogen come from? Well, it came from the fact that there was always one more hydrogen here. I just didn't draw it because it wasn't part of my reaction, and it was here too. So the entire time that hydrogen was there, it just wasn't reacted. And now this is the Onley hydrogen that's left over because both the chlorine and the hydrogen that were originally in that position both left. All right, so that's how we get an AL kind from elimination. It turns out this is gonna be one of the only ways to make all kinds. So it's important that you guys pay attention to this and know how to use this reaction. Okay, Now I want you guys to do the whole mechanism for the second step, and then I'll go ahead and show you guys how to do it. Not for the second step, for the second reaction. So go ahead and try toe work on this one as well. Let's do it.
Supply the mechanism and product for the following reaction.
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example
Supply the mechanism and product for the following reaction.
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in this case, we started off with what we would call a gem die. Hey, Light or Germinal die! Hey, lied because, as you'll notice, both of my bro means air coming off the same carbon. Now, in order to conclude that we could do a double D hydrology nation on this, we just have to make sure that one of the beta carbons has at least two hydrogen on it that can react twice. And it turns out that this one is my beta carbon toe, both of them. And it has two agents. Okay, well, what would have only what would have happened if I only had one age instead of two? Well, if you only had one age, then you could Onley eliminate once. Okay? But in this case, since I have to, I will be able to do this double d hydroxyl origination. So let's go ahead and get started. L d A. As we know, is a very strong, bulky base. It's gonna pull off these hydrogen. Um, what LD actually looks like in case you want to actually draw it out is like that with a lithium. Okay, so we could just go ahead and use that version of L D. A. To pull off these hydrogen. I would grab one of the HSE, make a double bond kick out the bro. Mean, what I would wind up getting is a new double bond and of roaming. Okay, so that's my product. After one equivalent, can we keep going? Yes, we can, because I still have Ah, hydrogen left. Okay, so now we're gonna use my second equivalent of L D. A. To pull off this one. And what I'm gonna finally get is a triple bond. Okay, so I got a triple bond. Plus, I get, you know, two of the LDS with h is on them, and I get to bro mean and ions. Alright. So that wasn't so bad. I hope it's very related thio e to now, what's just important to know about this is that this is one of the only ways to make all kinds. So whenever you're thinking of making an AL kind or an Alka nine, which we're gonna talk about more about, you're thinking How can I do a double D hydrology nation? That's what you should be thinking, at least for Orgel one. All right, so let's go on and move to the next topic.