Organic Chemistry

Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.

5. Chirality

Chiral is the chemistry term we use to describe objects whose mirror image is different from the original. 

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  • The mirror image of any chiral molecule is called an enantiomer.
  • If a molecule has an internal line of symmetry, it will have the same mirror image (achiral).
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concept

What is chirality?

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one of the ways to see if two molecules they're gonna be related to each other as stereo I summers is to look for something that we call Chire ality. So what is Kyra ality? Well, what kind reality says is this? Pirelli says if you look into a mirror and you get a different image than the image that of yourself, if you get a slightly different image and opposite image, then that means that you're gonna be a Cairo compound. That means that that image is going to be Cairo and it's gonna be different. And what we call that image is called non super imposible. Non super imposible is a really confusing way of just saying a different image. Okay, so I could give you a few different examples. So for example, um e look at my face in the morning when I see my face in the mirror and I'm brushing my teeth, it looks a lot like the face that I actually have. Okay, and that's because there's a line of symmetry in my face. So when I get the image back, I see the same exact image. Okay, so that would be something that that is called a Cairo because the images the same coming off of the mirror or at least it should be mostly the same as my face. Okay, Another example. That of something that is different would be like my hand. So my hand, I put it up against the mirror. The image I get is the opposite image. Okay, So that means that if I were to cut out the image that I see in the mirror and put it over my hand, I would get to opposite images. Okay. And that's the idea behind Chire ality. What Kyra Ality says is that if you get on opposite image when you look in the mirror, that is a Cairo compound. Okay, now the name for that different image. It has a really funky name that you're just going up to. No, and it's called an anant humor. Okay. And I could get really fun, depending on what your professors accent is like. But in Antium, er just means it's the mere image of a Cairo compound. Alright, So literally it could be anything. It does not to be a molecule. It could be ah, person. It could be a car. It could be Ah, cat whatever in an anti murders, just the mere image that's different. Okay, so here, let me show you guys an example with an actual molecule. Here's a molecule and what I want to show you is this, like, fake mirror that I drew. It's just this dotted line here. So imagine that this molecule, like I said, maybe it's like brushing his teeth in the morning. And it's looking at itself in the mirror. Okay, so has an eyeball. Obviously, this is just a really cool molecule. Alright, so it has an eyeball on. What does it see? Well, what it sees is okay, Well ah, lot of these. Ah, lot of the image looks the same. For example, what it sees is that the amine is towards the top. Okay, this is Let's say that's it's hair. Okay, so it's hair is at the top. He thinks everything is good so far, all right. And he also sees, for example, notice that I have some wedge and dash notation where wedge has to do with something. Being in the front and dash has to do with something being in the back. Okay, That means if this is a three d image, the dash should be behind and the Wedgwood be upfront. Okay, so what he see Is that okay? The hydrogen is still in the back. Cool. So this one is still in the back? Well, you know, everything looks fine, but then you notices Something's weird Where you notice is that well, the oh, age used to be on the right side, but in the image that he's looking back, the O. H. Is actually on the left hand side of himself. Okay, so it's like his hand or something. His hands on the other side of his body and then the same way with the metal group. The metal group used to be on the left, but now it's on the right. Okay, Now, I know this seems normal to you because you're thinking Oh, yeah, This is a mere So that means everything's gonna be flipped. Johnny, this isn't This shouldn't be new to you. This is just what happens when you look into a mirror. Alright. But that's all your professor wants. You know what your restaurants, you know, is that some molecules when they look in the mirror they're going to get that opposite image. Okay. What non super imposible means is that if I were to take a cut out of this thing, Okay, I'm gonna erase some stuff here so it becomes more clear I race the eyeball boo. Okay, when I take a cut out of this thing and lay it over this one, is it gonna look exactly the same? And the answer is No. Because even though the N H two would be in the same place and even though the age would be in roughly the same place because they're both facing towards the back, what I would get is that I would get O H over here, and I would get a C H three over here. And what that means is that these air non superimposed because my groups are in different places if I label overlay them over each other. Okay, so it turns out that we have a pretty easy rule that we can follow to test to see if something's gonna be Cairo or not. This is not the only way to figure it out, but it's just it's just like a rule that I already kind of hinted at. Which is this. If a molecule has an internal line of symmetry or anything, if anything has an internal line of symmetry, then it will have the same mere image. And if you have the same mere image, that's what we call a choir. That means it's not Cairo. It's not a Carol compound.

Draw the mirror image of the following molecule.

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example

Drawing Mirror Images and Determining Chirality

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So let's go ahead and do this example Where Let's just do this is free response. We just wanna work through this together and see if we can figure this out. It says here, draw the mirror images of the following molecules and determine if the mirror images the same or if it's different. Okay. Then after we do that, we want to figure out Is there an internal line of symmetry? And if there is, let's go ahead and notated. So for this first one, what I wanna do, you guys can just follow along. I want to draw my fake mirror again. Okay? And that's just gonna look like this. It's kind of ghetto. Okay, so imagine once again that this molecule is looking into the mirror. Alright. It's not even like a perfectly straight mirror. Whatever. What is he going to get back? What kind of image is he going to get back? Well, what he's gonna find is that Okay, there's a six member ID ring in the mirror. So let's write that down. Okay? And then in this first image, the bro means, Imagine that the bro means air like something on his face. They are on the right hand side, but for the mere image, they would be on the left hand side. Does that make sense? Okay, so, man, I'm not. That's a really ugly bond. Okay, So are you guys getting that so far? So that would be our mere image notice that they're both still facing towards the back. Now, what I want to know here is is this mere image the same as the original molecule or different from the original molecule? What do you guys think? The answer is that it's exactly the same. And it's not because it's the reverse, the reverse if the reverse has nothing to do with it. What has to do with is that if I flip this around, if I rotate it a little bit, then I'm going to get the same exact thing. Now. I told you guys, I'm not going to do a lot of rotating. Okay, But for this part, just to illustrate this, I want to show you so if I rotated this molecule like that if I rotated it actually, 180 degrees to the right. Okay. I like to call that rotation like a a deejay spin. Okay, where I imagine that the vinyl record and just like spinning it around. All right, so if I deejay spin that molecule, what I'm gonna wind up getting is a molecule that looks like this. All right, So is that the same molecule, or is that a different molecule? That is the same molecule. Okay, so does that mean that this molecule is Cairo or a Cairo? What do you think? What that means is, if, since it's the same, that means it's a Cairo. Now I want you guys to look at is try to find Is there an internal line of symmetry in this molecule? Okay. Is there a line you could draw that would split it perfectly in half? And the answer is yes. There's actually an internal line of symmetry right here. Okay, If I were to take scissors and I would cut it in half like that, what I would find is I would get to perfectly symmetrical haps. All right, so remember that I said, if it has an internal line of symmetry, then it's gonna be the same. Okay, I'm sorry. It has an internal line of symmetry. Then it's gonna be the same. So it's gonna be a car. So all of that works out cool so far, you may be asked to draw images on your exam.

Draw the mirror image of the following molecule.

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example

Drawing Mirror Images and Determining Chirality

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So let's do this. My mirror would look like this. What I would wind up getting is a five member ID ring that looks like that. Okay. And I would get that The siege three up here is now on the is now going this way. And then the one on the dash is not going this way. Cool. Awesome. So now those are that's why mere image. So I'm wondering the same exact question. I'm wondering. Is this the same molecule? Alright, so let's go ahead and do the same exact thing again. Let's do a deejay spin 180 degrees and figure out if this is the same molecule. So once I do that what it's gonna look like is like this. I'm going to get the ring facing the same way originally. But now notice that this bottom group that was facing towards the dash now moved up. So that means that now I have a dash facing up. I noticed that the one on the wedge now rotate. It's now. It must be going down. All right. So is this the same molecules? The original one? What do you think? It turns out that this is a different molecule. Okay, This one is a different molecule. Why? Because there's actually no way that I could rotate this molecule for it to become the other one. I know you're in disbelief. I know some of you guys are thinking, Hey, but what if I flip it like this? Or if I flip it like this or if I rotated a bunch of different ways, couldn't become that never You can actually never turn this one into that one, no matter how hard you try. Okay, So these air different compounds. So that means that after the mere image is gonna be different. So that means that this is a Cairo molecule. Does that make sense? And then Cairo just means that I'm getting a different mirror image. Okay. What is the name of this mirror image you guys remember I told you is that it has a special name. Kind of funky in an summer. Okay, you guys air already learning a lot. Okay? And we're like, we haven't even really gotten into it yet. I'm just introducing this. All right. One more thing. Is there a line of symmetry? Is there a line that if I cut it down the middle, I'm gonna have to perfectly symmetrical halves on the original molecule. And the answer is no. Because if I went ahead and I drew this line of symmetry again, would I get to perfect tabs? No, I wouldn't. Because one side would have a metal going up once. I don't have a method going down. They would not match perfectly. So I'm just gonna right here. And you guys should put this in your nose. I'm going to stay here. No internal lying of symmetry. Wow. Okay. And what does that mean? If I have no internal line of symmetry, What that means is that it's Cairo. Okay, so we can use that simple rule, and we can figure out if something's Carol or not. Now, the whole point of this is to show you guys to prove why the internal line of symmetry is important. Do you see that now how? If it does have one, you're gonna get eight. Carol, If it doesn't have one, you're gonna get Cairo. But now that we understand this, do we have to go through this mere image crap every time? No. Instead, we can just look for a line of symmetry, and that's where I'm going with this. All right, so let's go ahead and move onto the next topic and we're gonna talk about line of symmetries.
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