Draw the inscribed polygon for the following molecule.

Question

An octagon inscribed in a circle, illustrating the Frost Circle for aromatic compounds.

Accepted Answer

Hey everyone. Let's take a look at the following example question. Here it says, 1st circle the 2 monosaccharides that will produce identical aldauric acids upon treatment with nitric acid. Then, label the products of these oxidations as optically active meaning chiral or optically inactive meaning achiral. Alright. So let's do the first part. We know that treatment of these monosaccharides with nitric acid is gonna oxidize not only their aldehydes, but also the primary alcohols on the bottom. So these aldehydes, we're just gonna say they're all gonna become o h groups. So let's work on showing that. So all of these will become o h groups, and then all of these down here will become carboxylic acids. So we'll have a carboxylic acid, carboxylic acid, same here, same here. And then down here, we'll have our carboxylic acid. So their goals are products or diacids that are created from oxidation with nitric acid. We have to look to see which ones would be identical. Here, it's not as easy to see both. So we had all of these monosaccharides. And if we take a look, we have L glulose, which would underwent this oxidation to create this structure. And we have D glucose, which is our first structure, it undergoes oxidation as well. It may not look like it, but they're actually identical. So let's just imagine that we took this and we flipped it. So the top part comes down here and this bottom part gets rotated up here. Doing that gives us what type of image? Well, if we flip it that way, let's draw what we would get. We get this carboxylic acid up here and then let's draw the rest of it. And then we get down here. So I'm flipping it this way. Alright. So when I flip it this way, these o h's now, they're gonna be over here because I'm flipping it that way. Alright. And this h would be here and this o h would be down here. And flipping it that way, we would say that these hydrogens after we've flipped it, they would be up here, and then this o h would be down here, and this h would be here. If you look at that, what does that resemble? This structure here resembles this structure right here. So upon strong oxidation, we would say that the products, the oxidized products of the glucose in l, gulose, will be identical. So that's the first part of this question. We couldn't do that with either of the monosaccharides in the middle in the form of l galactose or d mannose. Right. So we're gonna say here for this first part, it's the d glucose plus the l, gulose. Now, looking at our carboxylic acids that we've created, our dark carboxylic acids, let's let's answer this next part. It says, then label the products of these oxidations as optically active, meaning chiral or optically inactive. Now, to be optically inactive, where where are the scenarios that help to create something as being optically inactive and therefore achiral? Well, first, they'd have to have either no chiral centers or they'd have to be a meso compound. The first one is out of the question because all of these have chiral centers. All 4 of these monosaccharides even in their oxidized forms would still have chiral centers. So we're not looking at that. What we're looking for is which one represents a meso compound. Remember, a meso compound has an internal plane of symmetry. The way we can check this is just cut these diacids down the middle and look, do we have some type of internal plane of symmetry? Does the top portion match the bottom portion? If we take a look, let's look at this top portion here. This top portion, doesn't look like the bottom portion. So let's make this one 1 and this one 1, and this 2 and this is 2, and this is 3, and this is 3. Okay. So the ones are the same, but that's not a reference to a chiral center. 2 and 2. Alright. So we would say that yes, both of them have an o h on the right so they are modeling each other. But then, if we look at these as threes, they don't match up. It's not looking in a mirror. This o h is here, so there'd have to be an o h here. So there is no internal plane of symmetry and therefore this is not a meso compound, meaning that it will be chiral overall and optically active. Let's go to the next one. Here's our mirror here. Let's look in the mirror. So we have 112233. Looking in this mirror, there's an o h here And for 2, there's an o h here. Okay? For 3, there's an o h here and there's an o h here. So this thing is looking at itself in a mirror internally and it's seeing itself back, its own reflection. So there is an internal, bit of symmetry within this within this, oxidized form of L galactose. So in its diacid oxidized form, we would say that it's optically inactive because it is a meso compound. For the next one, 112233. Looking into the mirror, for 2, there's an o h on the right, but for this 2, it's on the left. So it doesn't match up automatically. It can't be a meso compound, so it's optically active. And then finally, this last one, 112233. Looking in the mirror for carbon 2, it sees an o h on the left. There's an o h on the left. Okay. For carbon 3, this one has its o h on the right. Oh, but this one does not. So there is no internal plane of symmetry where the top part matches perfectly with the bottom part, so this could not be a meso compound and therefore it's optically active. So going back to the beginning of this question, we would say that the 2 monosaccharides that form identical aldauric acids upon oxidation with nitric acid would be d glucose and l gulose. And we would say that all of these diacids, their oxidized forms, are optically active except for the diacid form of L galactose. If we cut it right in the middle, we would say that the top part and the bottom part match. There's an internal plane of symmetry at play making this a meso compound and therefore optically inactive. Right? So just keep this in mind when you are faced with questions like this. Take a similar approach to determine if things are identical and whether they are chiral or achiral in nature. Doing this and applying these concepts will help you with questions further on.

Draw the inscribed polygon for the following molecule.

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