“How are the following two molecules related to each other?”
Does this sound familiar? This is one of the most important questions you will have to answer in Organic Chemistry 1.
Definition of Constitutional Isomers
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What is a constitutional isomer?
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So what are constitutional ice MERS their compounds that have the same exact molecular formulas, meaning that both the compounds will have all the same atoms in them. But what is different about them is their connectivity. So go ahead and write that down connectivity. What does that mean? Connectivity has to do with the way the atoms are bonded to each other. So, for example, of my first molecule has Adams a linked to be linked to see or bonded to A B and C, My second molecule might have the same Adams A, B and C, but they're arranged differently. So maybe is connected to C and then see is connected to B. That would be an example of a constitutionalism. For this course, what you're gonna have to be able to do is you're gonna have to be able to look at two different compounds and tell, What is that relationship? Are they the same compound, meaning that everything is exactly the same in terms of the molecular formula and the connectivity? Or are they completely different compounds, meaning that they have different atoms all entirely? And then there's this other category, which is are they constitutional ice summers, which means that they have the same atoms, but they're connected differently and it can be really tricky. Thio differentiate which one is which? That's why I have made this nice little flow chart for you guys to follow. All right, so
Constitutional isomers are molecules with identical atoms but different connectivity.
Constitutional Isomer Flowchart
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Using the flowchart to determine isometric relationships.
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so imagine that you're given this question right here. This is the This is an exam. How are the following Two compounds related. Are they identical constitutional ice, summers or different compounds? Where do you even begin? Well, it turns out that this question is, I think a little bit beyond your level. All of you guys are probably a little bit stumped by this question. You might think that you know the right answer, and you might be right, but most likely you didn't get to the answer in a systematic way. So I want to teach you guys is the systematic way to get these problems right every single time. All right, so we're gonna come up back up to that question. But what I actually want to do is go through these steps right here on these steps, will guide you through constitutionalism or questions, okay, And notice that it uses I h d. That's why I had to teach you the HD first because that's the easiest way to tell the difference between different types of compounds. So my first question that I have to have to ask myself makes sense. It's just are all the atoms the same. Okay, because remember I told you that in order to be a constitutionalism, all the atoms have to be exactly the same. So the way that we tell a lot of students, what they do is they start counting every single atom, all in in the entire molecule, and they compared to the other one. And then obviously they see if they're the same or not. But what I What I would recommend is don't count the hydrogen. Okay, Count on Lee non hydrogen atoms and then count the HD in both compounds. The reason why is because I HD is actually just a measurement of hydrogen. Remember that ihe would tell you how many hydrogen zehr missing. So and I HD happens to be much easier to calculate the number of hydrogen. You know why? Because if you have to calculate number of hydrogen, that means you're looking at a bond line structure. You're gonna have to first put all the hydrogen in there and then you might have so many hydrogen is that you might miss count. And that happens all the time with students. So what I prefer is hey, instead of counting each h out at a time. Just use the HD instead. The HD is a placeholder for a number of hydrogen. So now check this out. If those two numbers are not exactly the same. So if I have a different amount of non hydrogen atoms or a different amount of I h d in both of the atoms in the both of the molecules, then these were going to be different compounds. Why are they different compounds? Well, because if they don't have the same atoms, then they're just automatically different. Okay. Ah, compound can only be the same as another compound if it has the same exact Adams inside of it. Okay, So that would be the answer for this question. Appear if we found that they had different amounts of carbons, which is a non hydrogen atom or different amounts of HD, But let's keep going and see what happens if they happen. Toe lineup. Meaning that the non hydrogen atoms and the HDR exactly the same in both. Then we go to step two. Okay, what is Step two will step to make sense as well. Now I'm gonna ask myself. Are all the atoms connected? Exactly the same way. Okay, Now it turns out that most of the time this is gonna be a very easy question to answer. Most of the time, you're going to see your two compounds, and they're gonna look very different. For example, one of them is a square, and one of them is a four carbon chain. Would that be the same thing? Would it be the same thing if I had a square on one side for carbon chain on the other side? Would you say that they're connected the same way? Absolutely not. They will completely different. The only way that they could be connected. The same is if every atom is connected to the same Adam on the other molecule. Alright, so most of the time, common sense is just gonna tell me yes or no. Either they look the same or they don't. But sometimes you get a situation like up here where these two molecules above me, they look like they're kind of similar, but maybe they're rotated. I don't know. Okay, so for this one, we're gonna want to use a systematic method, okay? And what I always say is, toe look for what I call a landmark Adam. Okay, now, this is not a word that you're gonna find in your book, so don't look for landmark. Adam isn't anything. It's just a word that I used to say. Look for something that stands out. Okay. So you would look for something that stands out that you can compare to everything that you can compare in both molecules. Okay, So, for example, maybe if your compound has an oxygen in it, then you would look at where the oxygen is in the first one and where the oxygen is in the second one and see, Are they in the same place? If your oxygen has I mean, if your compound has something else like a ring in it, maybe you look at the ring and you say, Is the ring in the same place in both? Okay, if they're not exactly the same thing, that means that you have constitutionalism. Er's why? Because that means that we got to step two, which means all the atoms in the HD was the same. But then step to. What we said is that they are not exactly the same in the way they're connected. So that's constitutional items. That's the definition of a constitutional I summers of other constitutionalism. Er okay, what if they are the same, though? So let's say that means that now all my atoms are the same and they're connected exactly the same. Then those were just going to be identical compounds. Does that make sense? And those are my three options.
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Isomeric Relationships
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I want you guys to do, we're going to do the first one has a worked example, and what I want you guys to do is work with me. Think through this. Where do we start with these two molecules? And maybe, let's just call this question A What would we start to compare them? First of all, it's saying, How are they related? Are they identical? Are they constitutional or are they different? I know right away there's one answer. Choice that we can eliminate. What do you think? Which one can we eliminate right away? Identical. These air, not identical compounds. One of them has a ring and one of them is a chain. There's no way that those are the same thing. Wouldn't you agree? So we're just going to scratch out identical. It's not even think about that now. What I want to do is I want to go through my flow chart. Okay, so the first thing I do is I count up non hydrogen atoms and I HD Let's start off with non hydrogen atoms. What I have here is carbon oxygen and flooring. Would you guys agree? I also have hydrogen is present But remember, I'm going to ignore those for now. So how maney carbons do I have in the first molecule? Good. I have five. 12345 How many oxygen's do we have? One. How many Floridians do we have? One makes sense so far. Now I'm gonna do the same thing for the other one. Carbons. Oxygen's Florian's How maney carbons do I have also five. How many oxygen's do I have? One. And florins one. So far, it looks like all the atoms are the same. Okay, so it looks like maybe these air constitutionalism, er's. But let's also count HD. Remember, Have to count HD. So the HD of this first one. Just remember, when you have a structure, how do you count? I g remember that double bonds and rings equal one and your husband's equal to. So in this case, what's my I HD? It's one. Okay, now let's take the HD of the second compound. What's the issue of the second compound? Zero. Are these PhDs the same? It's zero because there's no ring. There's no double bond. There's no triple bond. So are these HD is the same. Know what That means is that remember what it means for a night HD. It means that you're missing to H is. It means you're missing two ages. So do these two compounds have the same number of hydrogen? No one has less than the other. So what are these going to be? Different compounds? Okay, because I got stuck right up here, if not exactly the same. They're different compounds. That's exactly what happened. The eighties were not the same. So I had different compounds. Does that make sense now? The reason that I went through this whole trouble of teaching I HD is because as our molecules get bigger, that's gonna be even more and more helpful. Instead of having a count on every single hydrogen we just use I HD and it's so much easier, okay?
Are they different molecules, constitutional isomers, or identical?
Pair A
Pair B
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Isomeric Relationships
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All right. So first of all, there's another one that we could immediately cross out. And again, that was identical compounds. The first one has a triple bond. The second one is a square. There's just no way that these things are the same. So now let's talk about carbons and nitrogen. So how maney carbons does this one have four. How many carbons does this one have? Four. How many nitrogen is? Does this one have one. How many nitrogen is? Does this one have one? Are there any other non hydrogen atoms? No. I just have carbon, nitrogen and hydrogen. So I'm done with that part. Now I just have to do the HD. So what's the, uh what is the I h d? Wow, What is the HD of the first molecule? It's too. Why is it too? Because remember that double Bonds count is one triple bonds count is too. So I just did three triple ones. Count is two. All right, so that means that it's missing four hydrogen. Let's see if the other one is the same. My HD over here is I have a ring and a double bond that's also going to be equal to two. That means that this one is also missing four hydrogen, which means that these have the same atoms. Okay, so I'm just gonna put here. Same Adams. Okay, so now that I just found out that these have the same atoms, Alright. Are they connected the same? No. We just said that they are not connected. The same one has a square one has a triple bond. Their way different. So the answer has to be constitutionalism Er's. And I could tell that a lot of you guys got that. So very good. Hopefully that makes sense to you guys. This is just the formula that the general structure that used to solve these problems I hope that this systematic way will help because it can get confusing the way that these compounds with very similar okay.
Is there a choice we can rule out immediately?
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Isomeric Relationships
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All right, so this one was tricky. Alright. But what I want to show you guys is, first of all, let's count up the HD and carbons. So carbons for this one was 10 and carbons for this one was 10. Okay, Now, if we calculate the HD, the H d for the first one is zero. There's no double bonds. There's no rings. There's no triple bonds. The HD for the second one is also zero. Okay, so what that means is that these have the same atoms, Okay? Now all we have to do is figure out. Are they also connected the same? Okay, in this case, I said this one's tricky because I need to find a landmark. Adam, I need to find an atom that I can compare in both of these and see if it's connected the same way. What I would choose here is I would choose the atom that has four bonds on it because notice that I have only one carbon that has four Barnes on this entire thing. If I can locate that one on both of these, then I could compare what are the four things that are attached? So over here. If I'm looking for the atom that has four bonds, it would be right here. Okay, So now what I do is I'm gonna look at the four things that are attached and see if those same four things are attached to the blue carbon on the other side. So notice that this blue carbon has two methods coming off of it. Does the other blue carbon have to? I'm sorry. And that's called a methyl group. But we'll talk about that more later. Like you don't need to know that that's called a methyl group. But for right now, you do need to know that that's a ch three. So I'm just gonna make this a little bit bigger. Ch three ch three. Okay, so we have two ch three is coming off of that. Do we have the same thing coming off of the other one? Yes. Ch three ch three. Cool. So then what else? Well, we also have a carbon chain that has three carbons. 123 and it's connected in the middle. Okay, Now look on the other side to see if we can find the same thing. Actually, yes, we have one that has three carbons and it's connected in the middle. So so far, this is looking like it's the same compound. But let's just look at this last one. So this last one looks like it's four carbons, Um, 1234 And it has that pattern where basically it's connected. Toa ch two and then a c h and then two ch threes. So basically, I have this pattern of siege to ch and then c h 32 Do you guys see that? I'm just using the condensed formula. Okay, so now let's see if I get the same thing on the other side. On the other side, I have a CH two connected to a C H and then connected to C H 32 It's the same exact thing on both sides. It's just now. I just drew the condemned structure, the attendance formula going the other way. All right, so it turns out that these molecules are exactly the same. They were just rotated in different ways. All right, now, I don't want you to try to visualize. Oh, if I flip this, it would be that I just want you to know Hey, they have the same groups on all sides. So these would be identical compounds because they have the same atoms and they have what we call the same connectivity, okay?
So now you should have a pretty good idea of how to solve questions asking for molecular relationship.