Meso Compounds- This is the Second Part, So Enjoy. Do you want to First Part Click Here
Meso Compounds-How we have a mirror image on both sides.
So we said the hydrogen is going to be going into the plane of this page, where’s the oh ah, is going to be pointing out because it used to be pointing in. But as we rotate the single bond, it’s going to come out. So notice in Meso Compounds configuration right over here, if we draw a straight line down the middle. Notice how we have a mirror image on both sides. So there’s a plane of symmetry because all the groups align the hydrogen with the hydrogen. The alcohol with the alcohol, and then your methyl group with the methyl group. So this structure right over here, at first glance, even though it doesn’t look like it. Meso Compounds has a plane of symmetry, but you have to remember that with a single bond, you can rotate that sigma bond.
So Meso Compounds satisfies both criteria.
It has stereocenters and a plane of symmetry. So we would call this Meso Compounds a musical compound. So here’s a very common test and the exam-like question that you’re going to see. Notice this carbon right over here, they have not indicated the stereochemical relationship of the groups. What I mean by that is the chlorine is not pointing out in a wedge, or into the plane of this page.
We know that there are four substituents around that carbon. Notice, here’s hydrogen, a chlorine methyl group, and this last group, Meso Compounds the last portion is the fourth group. So we know there’s a stereocenter. For those exact same reasons, we know that there’s a stereocenter, right over here in purple. So we satisfy criteria number one, that there are stereocenters. In order for us to identify the Meso Compounds, we first have to draw all the stereoisomers that are possible.
Power of N
Remember, Meso Compounds equation two to the power of n with the N is the number of stereocenters. So in this case, Meso Compounds’s two to the power of two, because we have two stereocenters. So we know at max, we only have four stereoisomers. This is the max number of stereoisomers. Now when we take a look at these two carbons right over here, right, now, when we take a look at these two carbons right over here, one possibility is the chlorines, both pointing out. So in case of a, so in a both of the chlorines are pointing out, I’m just going to label this carbon one and two, so it’s easier for us to follow. Now another option is that at carbon one, and two, both of these chlorines are pointing into the plane of this page with these dashes.
A third option is that one of the chlorines pointed out like in this case right over here and see one of the chlorines point out, where’s the chlorine at number two points into this page. And then a final option. So here’s carbon One, and two is that we have on carbon number one, the chlorine pointing away. Whereas on carbon number two, we have the chlorine pointing out at us. So there are four possibilities. Let’s go through the relationship of these four groups, and then take a look at which one is the mutual compound. So let’s talk about structure. And B, we’re first going to see if any of them is a mutual compound by satisfying those two criteria.
How to take relationship between these two
And then we’re going to take a look at the relationship between these two. Well, let’s start off right here. We know that these two are stereocenter, we know that they’re attached to four groups. But if we go ahead and cut this plane right down the middle right over here, we can see that the left-hand side is not equal to the right-hand side. Well, a lot of you may be sitting there and thinking Can I rotate this because Meso Compounds’s a single button. So let’s rotate that, when we’re rotating this, I’m going to hold this side the same. So this side with the carbon, the Korean, and the methyl group. Let’s keep that the same in Meso Compounds.
So let’s hold that side the same, so I’m just going to rotate it on Meso Compounds. So notice right over here, okay, so here’s the chlorine. And then on the other side, when we rotate this right over here, the chlorine used to be on the bottom, but it’s going to come towards the top. But when it comes towards the top, remember that Meso Compounds used to point out at us, it’s now going to be pointing into the plain of this page. So here’s our chlorine right over here.
Notice this is the chlorine, and then this group, the methyl group is going to come down. When we draw this plane down the middle. Again, we can see that these two are not symmetric on Meso Compounds. Because, on this site, the chlorine is pointing out at us. On the other side, the chlorine is pointing into the plane of this page. So there is no internal plane of symmetry. So we know that this is not a Meso Compounds structure.
What about the relationship between these two
So for the exact same reason, these two are stereocenters right over here, but no matter how we rotate the single bond for the exact same reason as a, we can never get an internal plane of symmetry. So we know that these two are not Misal.
Now, what about the relationship between these two right over here. So, you take a careful look at this right? And if you go through and you assign your RNs configuration, notice this is actually our n AR, whereas in this structure on the right-hand side, this turns out to be s n s,
you can prove that at home go through and practice but I know that these two are opposite stereochemistry. How do I know that? Well in this carbon, the chlorine is pointing out at us in the other carbon the chlorine is pointing in they have to be different.
Whereas in Meso Compounds structure, the chlorine is pointing out in Meso Compounds structure, the chlorine is going in assigning the ends just helps solidify my knowledge, Meso Compounds helps me confirms that both of these stereocenters are opposite. So notice this one. And this one, if you have the opposite configuration at every single stereo Center, the relationship between these two groups is an inter MERS. So remember, these two are NAND tumors.
Now, what about structures C and D?
First, let’s go through and see if they’re Meso compounds, starting with C. So notice right here we have a stereocenter. Right, we also have another stereocenter. So that’s criteria number one, it has stereocenters. criteria. Number two, let’s see if Meso Compounds has a plane of symmetry. If you first start to draw a plane down the middle right over here, notice the left-hand side is obviously different from the right-hand side. So we know that’s not the plane of symmetry yet, what we’re going to do because this is a single bond, I’m going to rotate about Meso Compounds single bond.
Meso Compounds single bond
Before I rotate, again, I’m going to hold this side exactly the same, I’m not going to change that side. And then what I’m going to do is I’m going to rotate Meso Compounds single bond. So let me go ahead and draw that first. So on this site, on the left-hand side, we’re going to keep Meso Compounds the same, right, this is chlorine, this is a methyl group. On the other side, notice that when I rotate, the first thing is this chlorine, it used to be on the bottom side, but it’s going to come towards the top, Meso Compounds used to be pointing into the plane of this page.
But when it comes towards the top, Meso Compounds should be pointing out at us. So that’s what we’re going to do, we’re going to draw that chlorine. So notice that the chlorine came up, right, chlorine comes up here, and it’s pointing out at us. Now, the methyl group right over here, this methyl group used to be on the top side, as we rotate this, it’s going to come towards the bottom. So now when we take a look at Meso Compounds structure, notice
How there’s Meso Compounds perfect plane of symmetry
So Meso Compounds satisfies both criteria. Number one, Meso Compounds has stereocenters right over here. And then number two, there’s a plane of symmetry. So we know this must be the Meso Compounds structure.
Okay, so by the same reasoning, D is exactly the same as C, right? So notice right over here, these two, if I just went and I rotated this bond right over here, and I kept this side the same, what I’m going to end up with is I’m going to end up with the structure.
So here’s chlorine, keeping that side the same. Remember, when I rotate this, this is going to come up. So this chlorine is going to come on the top side, and Meso Compounds’s going to be pointing away, and this methyl group is going to come down.
So we know these two are Misal right. But what’s the relationship of these two right over here? in this direction, notice that they look very similar. Okay, so I’m going to call this carbon one. And carbon number two, I’m going to hold this structure the same, so don’t do anything with this structure. Right now in this structure, can you see that the two hydrogens are pointing towards the back? So here are the two hydrogens, they’re pointing towards the back. Whereas in this structure,
We can see the two hydrogens, right?
The two hydrogens are pointing out at us. So what we’re going to do is we’re going to take this structure. And we’re going to rotate this entire structure 180 degrees. When we rotate it 180 degrees. So carbon one on this site, Meso Compounds are going to go over here.
I’m going to draw that. So when we rotate Meso Compounds, so notice carbon one comes. Here, and as we rotate carbon one to this side, carbon two is going to come back to this site, right. So just imagine this, take this rotated to the other side when we rotate this structure. Remember how the two chlorines are pointing towards the back, as we rotate it 180 degrees, notice the two chlorines.
So I’m just going to go back and use my pen to draw them in. So using blue right over here, the two Koreans are actually pointing out towards us. When the Koreans point out towards us, I’m just going to draw on the methyl group. The two hydrogens that used to point out as we rotated 180 degrees, the two hydrogens are going to be pointing in this direction, right over here. Okay, so the two hydrogens are pointing towards the back, we can now see that that structure looks exactly the same as this one.
So if you actually went through, and you tried to superimpose these two right over here, you’re gonna see that all the atoms overlap. We just proved that here. So in a musical structure, whenever you get a musical compound. You always want to make sure that you’re not repeating an additional structure. So this question had stated draw me all the stereoisomers that are possible. We would be omitting one of these to both of them are correct, but they’re the exact same structure.
So coming back to this example, the Meso Compounds first thing that we want to do. When we’re using this to the power of any equation, if you have a Meso Compounds structure, you’re going to minus one From that equation, therefore, you only end up with three possible stereoisomers. We said that three possible stereoisomers are a, b, right? And the Meso Compounds relationship between these two they are an antithesis to each other. Whereas structures C or D, are both correct.
But the Meso Compounds C and D are simply the exact same structure. So, if the question had stated draw me as many stereoisomers as possible, all you have to do is omit this one right over here. So, hopefully after going through all of those examples, you now have a much better understanding of what a mutual compound is, and how to identify them on tests and exams. Joining us and of course, crackers, guys, we hope that the article has been fun and helpful in your academic journey. We release content on a weekly basis, so don’t forget to subscribe to stay up to date. Our mission is to provide a world-class education for students everywhere.
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