Organic Chemistry

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8. Elimination Reactions

Solvents are (mostly) inert compounds that provide a medium for a reaction to take place in. 

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General format of reactions and how to interpret solvents.

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Alright, guys. So we've been spending a lot of time talking about nuclear files and leaving groups. But sometimes when you look at your reaction, you're going to see some weird letters at the bottom like you might see D m f or D M S o or even just water. And you're wondering, what kind of role does that compound play in this reaction? In fact, you might be getting freaked out like I don't know the what kind of reaction I have because I don't recognize this molecule. And I'm here to tell you that that is usually going to be the solvent. Okay, if you see something at the bottom of your arrow, that's usually where the solvents go. And that's why we're going to discuss in this page. So let's go ahead and get started. So solvents are basically inert compounds. That's the whole point. They can't react. Okay, the whole point of a solvent is that it's something that serves as a medium for you to run a reaction in. And even though they are, you know, they do have impacts on reactions to some degrees. What we're gonna find in this course is that the impact of your nuclear file and leaving group is much, much more important than the impact of your solvent. So typically, when we see solvent questions, it's gonna be in the form of a conceptual style question. We'll talk about what type of solvent is favored, but it's not gonna be a mechanistic question where it will actually determine the type of reaction that you have. Okay, so I just wanted to let you know, just underline this part that these solvents are rarely gonna affect the outcome of a written reaction so many times we're just gonna neglect them. We're not gonna look at them too much, Alright, So overall, if we're looking at a chemical reaction, because I know this is new to a lot of you guys we're gonna do is we're gonna see some kind of re agent or some kind of starting product, okay. And then you're going to see an arrow, and that arrow is gonna have to compounds. Usually it's usually gonna have something at the top, and that's usually the re agent. That's usually the active substance. Okay, then at the bottom, typically you'll see the solvent. The solvent is the thing that, like I said, does not react but just serves as a place for the reaction to occur. Okay, Now, what I'm saying right now isn't a written rule. So that means that there are gonna be times where maybe if you have a two step reaction that you'll have the on top of the arrow is one of the parts. And the second part is Azat the bottom and both the reactive. Okay, but really, what I'm trying to say is that many times you're gonna see reactions with solvents in them and really, it's mostly your job to ignore them. It's mostly your job to say, Hey, I'm not going to really pay attention to this part. I'm just gonna pay attention to what Johnny said was really important, which was the nuclear falls and leaving groups

Although extremely important in lab, they rarely affect the outcome of a written reaction in Orgo 1. In fact, for the purposes of this course, I will usually have you ignore solvents in questions requiring you to predict mechanisms.

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There are exceptions to the above reaction format. If reagents are numbered, several may be both above and below the arrow. However, many simple reactions do follow this format. 

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The difference between protic vs. aprotic solvents.

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So as solvents go, there's basically three general categories that they fall under. Um, the first would be polar solvents. Okay. And this has to do back with when we talk about die polls. A really, really long time ago. Um, you stopped to remember that polar solvents are just the same way that we determine what a polar solvent was at the beginning. When you talk about deposit the same thing here, it's a molecule that has a net dipole. So just go ahead and write that down. Okay, So molecules with net die polls would be polar solvents. Then we have two different types of solvents. We have a product, solvents and product solvents, and this I have to define because we never really used that word before. So basically, the essence of a product solvent is one that can hydrogen bond. Okay, so if you're able to donate hydrogen because you are oxygen, nitrogen or flooring, that will be a considered a product solvent. Okay, so you might already guess that a product solvent would be one that cannot display hydrogen bonding. Okay, so let's go ahead and write that down. And then that means that a product solvent is going to be a solvent that displays age bonding. Yeah, and that age bonding has a special property. It turns out that for different types of reactions, it's gonna have different effects. So for when you when you're making Carvel cat irons, if you can hydrogen bond, that's actually going to stabilize the Carvel Catalan and make it easier to generate a Carvel Catalan for that step. So be thinking about that, Okay? There's another thing that they do. They also tend to slow down nuclear files. So imagine the of this negative charge and you've got all these waters sticking to it. It's gonna make that negative charge a little slower through the solution and a little bit more difficult to donate its electrons. So it kind of has the same effect for both the positive charge and the negative charge. The problem is that for the positive charge, it's a good thing to stabilize it for the negative charge. That's a bad thing because it winds up hindering it and making it more bulky. Okay, so if we were to think about the type of solvents that we would use for mechanisms, we've learned forward mechanism. So far s and one s and two e one and a two. What kind of salt? What kind of mechanisms? What? I prefer to have a product solvent in. Okay. Think about a product. Means that means it can hydrogen bond. So what would be a good mechanism to have with the product solvent? Good. So would be one that has carbo cat ions. That would be sn one and e one. Are you guys following the logic there? Because products solvents are gonna be able to stabilize the Carvel cattle. And as I said before up here, Okay. And then that means that in an A product solvent, what would be a good mechanism to run? And that would be S n two and e too? Because these are mechanism that start off. Remember, the very first step is a strong nuclear fall attack, something So do I. Want a product solvent toe, bulk that toe, make it bulky. And to slow it down. No, I actually wanted a product solvent, so it's not gonna hinder it all. And just gonna zip right through the solvent. All right, So does that kind of makes sense. The distinction we're using. That's the kind of question that you could see a conceptual question on your exam. All right, so now what I want to do for the rest of this page is just go through these eight solvents and this will kind of be a combination of identifying solvents and also just a teaching moment for you guys toe learn a few comments, solvents that we use in all of organic chemistry, not just one. We're gonna use these solvents for Orgel one and for or go to. So we'll go ahead and we'll just do We'll just have a different answer for everyone. So you guys just go ahead and take your time with number one and figure out. Is it a polar, or is it polar product or polar a product? So basically have three options. You just have to check off one of the boxes. All right? And the way you're gonna look at that is look at the die pole and then determine if it can hydrogen bond or not. All right, so go ahead and try to figure it out

Polar solvents are solvents which contain a net dipole.

  • Aprotic Solvents are solvents that cannot display hydrogen-bonding.
  • Protic Solvents are solvents that display hydrogen-bonding (this stabilizes carbocations, but hinders nucleophiles)
  • Therefore, we will prefer to run SN1 & E1 in protic solvents, and SN2 & E2 in aprotic solvents.
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example

Identification of polarity in solvents

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Alright, guys. So did this molecule have a die poll? Absolutely. Remember that Oxygen's have lone pairs and those lone pairs have a depot pulling up. On top of that, we had die polls pulling up from the carbon. So we have a net Typo pulling up. So this definitely couldn't be a polar, right? Havel, Would it be? Would it be ableto hydrogen bond? Okay, so we know it's one of the polar ones. Would it be ableto hydrogen bond? The answer is no, because it doesn't have a hydrogen directly attached to an O. N or F. So this is what we would call polar a product. Okay, Um so as we discussed, this would be a solvent that would be really good to use for S and two or e too, because it wouldn't hinder that nuclear file. And this is actually a really common solvent in general. It's called Tetra Hydro. Fran, you don't have to memorize the full name, but you should know this is th f. So whenever you see th f, it's a very common solvent in or go. You should know that it's it's the cyclic ether, Basically. Okay, so and by the way. This is just for your own enrichment. Really? Like if on the test you forgot with th f looks like you could probably still get 100%. I just want you guys to get familiar with these guys because these were kind of like the usual suspects that we're going to see a lot and reactions. And it helps if you have some kind of context for what it is. All right, so let's move on to the next one.
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Identification of polarity in solvents

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all right, so this one was really easy. It definitely wasn't a polar. This would be polar pro Dick because it's just water and water means that has a DI poll and it's ableto hydrogen bond. Alright, so, honestly, like there's even, there's nothing I could say about it. That's just a super easy one. Let's move on to the next one.
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example

Identification of polarity in solvents

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All right. So if you drew this one out, where you would find is that there's actually a c tripled on N with a lone pair and then a methyl group. Would this have a net dipole? Yeah, it would. It would pull towards the lone pair. So that means that this isn't a polar. And is this ableto hydrogen bond? No. So this would be another version of polar a pro dick. Just You guys know this is a molecule called a CDO night trial, and it's not one of the most popular solvents ever, but it is something that I've seen before. So just so you guys know it doesn't have any fancy acronyms, but that's called acetone. I trial. All right, let's move on to the next one.
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example

Identification of polarity in solvents

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this one was a polar. Because if you draw it out, what you would find out is that even though we do have die polls, we have no net die. Poll. Okay, so this isn't even the right way to draw. Because remember, this is a Tetra Hydro all so really, the way I should draw it is with one of them facing towards the front and then one of them facing towards the back and then to on the plane. Okay, but what you would find is that they're all gonna perfectly cancel out, meaning that overall, this is a polar and a polar solvents. You don't have to worry about hydrogen bonding or not because they're never really gonna be ableto hydrogen bond. Okay, so that's just a polar. It's in a category of its own that's called carbon tetrachloride. You will see this later. When we get to the addition chapter, we're gonna use it for some reactions. All right, so let's move on
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Identification of polarity in solvents

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di Poll? Yes. Hydrogen bonding. No, this would be another polar a product. Okay, As you can see, there's a lot of polar A products. This one is called Dime Ethel sulfur oxide or just D. M s O. And once again, I wouldn't be teaching you this unless I had seen it literally 100 times in different textbooks. You're going to see D. M s so as a solvent. And now you guys just know what the react with the molecule looks like. Okay, I don't really care so much that you're able to reproduce it or draw it, but it's good just to be familiar that it's into polar a product. All right, let's keep going.
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example

Identification of polarity in solvents

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ethanol is easy. This one has a di poll and it's ableto hydrogen bond because the fact that it's an Asia attachment Oh, this would be polar product. Okay, in general, um, water and alcohol and a means will be your polar products. Okay. And that means it can hydrogen one cool next compound.
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example

Identification of polarity in solvents

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all right, So this is actually another common polar a product compound, and that is or solvent. And that is it's called Dime Ethel Former Meid or D M. F. Okay, so another one, it's another one that has this weird letters. And the reason that it's polar is because it has a lot of die polls. The reason that it's a pro dick is because there's no hydrogen is directly attached. To that end, If I had just had one h, that would be pro Dick. But these are actually methyl groups, right? Since their methyl groups, they actually can't hydrogen bond it all. So that would be a product. Okay, um and then finally, let's just do this last one.

The structure in the video and below is actually DMA since it's chemical formula is CH3CON(CH3)2.

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DMF would simply have an H instead of a CH3 coming off the carbonyl carbon to the left. Both would be considered polar aprotic solvents since no hydrogen bonding occurs.

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example

Identification of polarity in solvents

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Alright, guys, I actually gave this one away earlier. This one isn't a mean Okay, it's actually ammonia. So this would be polar pro dick. Why? Because it does have a die poll. You don't see it. That's because you haven't drawn it correctly. Remember that you have to draw nitrogen like a like a tribunal parameter, and it needs to have a lone pair at the top. OK, so there actually is a net die poll pulling up, right? I forgot to draw the ages and then all these ages air directly attached to end so it can hydrogen bond. Okay. And what I said earlier was that basically, if you're an alcohol, water or you're in a mean, you would be able to be polar products. So I'm just gonna go out of the way so you could see that I wrote polar product there. Okay, now my closing thoughts on the solvent area. I know it was kind of long because I give you a lot of examples. The whole point is this. No, that water alcohol Inamine are your products and know that everything was fancy letters like the alphabet soup of D m s O d h f or th f d m d m f All of those are going to be the A products. Okay, I really haven't seen a version of an acronym that is a product. So don't worry too much about that. Okay? So I hope that made sense to you guys. Let's move on to the next topic.
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