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Question 610 ptsRank the below compounds in order of their acidity. 1 will be the least acidic, 7 will be the most acidic )OHOHOHOHOH...

Question

Question 610 ptsRank the below compounds in order of their acidity. 1 will be the least acidic, 7 will be the most acidic )OHOHOHOHOH

Question 6 10 pts Rank the below compounds in order of their acidity. 1 will be the least acidic, 7 will be the most acidic ) OH OH OH OH OH



Answers

Rank the following compounds in order of decreasing acidity:

This is the answer to Chapter 17. Problem number 17 Fromthe Smith Organic chemistry textbook. Ah, and this problem asks us to rank thes three compounds in order of increasing acidity. Um and so, uh, actually, there are already, in order of increasing acidity. Um, but to actually make that determination, we need to look at what their contract basis they're going to look like. And so if we draw the continent based the 1st 1 here, um, we'll have a negative charge there. There's no resident structures. Um, so that's not going to be particularly stable if we draw the continent base of the second, um, molecule on, put the charge in the same place. We can see that it's a Lilic. And so it is resident stabilized. Um, so that's good. That's more stable on. And then if we do the same thing for the third molecule here, uh, what we actually see is that this molecule ah, when deep throat nated at the same spot, eyes going to be, um, aromatic. Ah, and so this is ah, a narrow Matic molecule. So obviously it's quite stable. Ah, and so again, they're already in order. So 12 three where one is gonna be least acidic. Ah, and three is gonna be most acidic on again. We made that determination by looking at the stability of the constant basis on That's the answer to Chapter 17 problem number 17.

This question covers qualitatively analyzing an organic molecule to determine the acidity or basis city of the molecule. To answer this question, we are going to be using an acronym called R. E. O. Which determines the order of each effect. Uh huh. That each of these effects has. They all stand for something that each of them has on determining qualitatively the acidity. So of a compound. So aliens for Adams, this is which adam is holding the is holding the acidic proton. Our chance for resonance is our conjugate base stabilized through resonance. I stands for induction. The inductive effect can be a stabilizing effect and it occurs when there is a highly electro negative hetero atom attached to a carbon of the on the molecule that is pulling electron density away from the acidic proton. And lastly it's gonna be orbital's. Um And each of these characteristics comes with very important and that's a hierarchical. So if we're looking between two examples and they're the same. Except for the acidic proton only has an in H. Vs. O. H. Then we would only look at which adam the nitrogen versus the oxygen um is the larger, more election negative nucleus. Now um option is more like the negative and smaller than nitrogen. So oxygen. The adam bearing the oxygen would be the more acidic um molecule. Um Now if both of them were ohh but one of them had a resident structure, another one did not have resonance structure and the one with the resonant structure. What happened in the conjugate base? So after you dip, rotated the content get basis stabilized by residents and that would be the stronger acid because the base is more stable and the country was more stable. If all those are equal then we would look to the inductive effect etcetera. So we have to rank three sorry, four molecules. So the first one is th three siege. Yeah see each two to each. And then we've got CH two. Excuse Me. Stage two. Okay so we've got our four molecules here and we see that. Let's go down the line for Mario. So the first thing we have to look at is adam, which adam has the most acidic proton. So this molecule it is here here here here. So we see that for each of these molecules they all have the same atom that's attached to the same proton. So we can move on to resonance. So do any of these have more resonant structures for the conjugate bases. Now the conjugal basically can just imagine without the hydrogen minus side here and we're not going to see any different resonant structures for any of these, they're all will be the same. So let's look at the inductive effect. Each Yeah molecule it's already we can see that these three molecules have some sort of inductive effect. From substitute electro negative molecule florian. These two chlorine, so this molecule up here would not experience any sort of inductive effect. Okay, so how does inductive effect work? Well, the closer that the electro negative adam is to the molecule or to the acidic proton, the stronger the effect will be. So we go 1212 we have a chlorine and fluorine that are two carbons over 12 from the proton. So thank you. Now we look between which of these is more electro negative. Flooring is more electro negative than chlorine is because as we know the taliban series, it's like this. Yeah. And we know that election negativity increases as we go up the periodic table. So florian is more electric than chlorine. As a result, we would say that so far are ordering one, yeah, two, three and last late before and the way that we got this again, remember through our E. O. We're only we're all else is equal. Except for when we get to induction, induction is a stabilizing effect, which means that if the conjugate bases stabilized with induction, that means that the molecule be more acidic. Now, we just have to assess only how induction affects each of these molecules. And we can see that this floral molecule here would be the most acidic, followed by the chloral on the second carbon, followed by final halogen ated alcohol here. Well, the final um Michael would be this. It's module here. All right.

This question asked us to rank the indicated hydrogen is in each of these compounds from most acidic to least acidic. And so we know that resonance will stabilize a base. And we can judge these hydrogen acidity based on the stability of their constant basis. So the contact base would be an an eye on if the loan hair on that carbon nestle carbon on and the more residents stabilization that it has from these carbon eel groups, Um, the better stabilize that base will be in there for the more acidic that hydrogen will be. And so I remember that the carbon over can only stabilize the carbon I And if it is right next to it, it's like this carbon. Uh, this one could be saved life by this carbon eel, but not by this one. So this one has one Carbonneau groups utilizing it. Um, looks it was in the contra bass. This one is has these sp three carbons in between it and each of these Carbonell works, So this one cannot be stabilized by either Carbonell Group and therefore is not very acidic since is very stable. This one, however, is stabilized by both of these Carbondale groups because their bull one bond away from it. So that makes this one the most acidic. Since it would have the most stable conjugal base, this one will be next. Since that is, uh, it is the next most stable conjugal basis stabilised one Karmiel group, and this one in the middle will be be at least, um, acidic, since it is an unstable contra bass compared to the other two.

This is the answer to Chapter 19. Problem number 47 Fromthe Smith Organic chemistry textbook. Ah, And in this problem were given these three molecules and were asked to order them from least two most acidic. Um, and then we're asked to give an explanation as to why. Ah, and so this, uh, middle molecule here is going to be least acidic. Ah, and as far as why it will be least acidic. Um, it's because ah, the car back silly gas. It is not substituted directly on the aromatic. Right? The car back Selic acid is separated from the ring by one carbon. And so Ah, this car back. So, like, acid is not much different than any regular alcohol carb. Oxalic acid. Um, we don't really get are the stabilizing effects of the aromatic ring. Um okay, so that's, uh that's the least acidic s o the intermediate, uh, acidity molecule is going to be this one. So inter immediate acidity. Um, and again, uh, with the car box, Silly gas. It's separated from the ring by one carbon. We're not really going to get the same strong affect that we would if the car about Selic acid were substituted directly onto the aromatic ring. But we do have the nature group on the ring, so there's gonna be some inductive electron drawing effect. Ah, and so this molecule will be somewhat more acidic than in the middle molecule here. The least acidic molecule. Oops. Say at least acidic. Um, and then so that the first molecule is going to be the most acidic. Um, and it's going to be the most acidic, Uh, four Two reasons. Really. So the car box silly acid here is substituted directly onto the ring. And so we have a ll of, uh, the the possibilities of drawing resident structures where we can, um uh Well, okay, so I'll actually just just draw this resident structure. So, um, the electron withdrawing effect of the para nitro group is going to increase the acidity here of the other thing and let me move these over. Okay, um is without drawing every every single resident structure that we could draw here. There is a resident structure. Once this this is the protein ated. So let me go ahead. And de Protein ate this. So it'll look like this negative charge there. Um, so there is a resident structure that we could draw where this molecule is going to look like this. So we would obviously have to move through some some residents structures in between. Uh, but there is a potential residents structure. Ah, where we have our car box Selic acid here while our core box late. I on rather here. Eso like that. Um And then we've We've moved the positive charge from our ah nature group. Well, eat. Okay. You know what? Um, sorry. Ah. Trying to be as as un confusing as possible. Um, and also trying to draw as little as possible. So Okay, so the nature group the night your group looks like this, right? And so this is how we conceive of a nitro group where one of the oxygen's has two bombs into lone pairs and no charge. And the other oxygen has one bond and three lone pairs in the native charge. And then the nitrogen has ah, positive charge on it. So this is what, um this is what our r d protein ated? Uh, Karl Marx allee gas. It would look like and so we could draw a resident structure for this where So we can draw a resident structure where both of these oxygen's have negative charges are the nitrogen still has a positive charge. This oxygen still has as negative charge from being Cipro nated. Uh, but we could, um, move, move electrons like this so these could go here thes could go here, and this bond could break. And so if we do that, we end up with a positive charge on this carbon. And so now, now we have positive charge in a negative charge that are closer together, and so they're gonna help to stabilize one another. Um, And so for, for all of those reasons, that makes this first molecule here by far the most acidic. Ah, and that's the answer to Chapter 19. Problem number 47.


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