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(24 points) (not all compounds have malch) Match the following i0 Iheir IR spectraNOz[374[6701532[776 `260ISmIO500 JOmJ0m2oI0IO...

Question

(24 points) (not all compounds have malch) Match the following i0 Iheir IR spectraNOz[374[6701532[776 `260ISmIO500 JOmJ0m2oI0IO

(24 points) (not all compounds have malch) Match the following i0 Iheir IR spectra NOz [374 [670 1532 [776 ` 260 ISm IO 500 JOm J0m 2o I0 IO



Answers

Match each of the $^{1} \mathrm{H}$ $\mathrm{NMR}$ spectra with one of the following compounds:

This is the answer to Chapter thirteen, problem number forty from the Smith Organic Chemistry textbook. And so this problem is giving us six pairs of molecules and asking us to identify what the differences would be in there. I are spectrums. And so for a we have a, um cycle Pantene Versace. Um, thiss out kind. And so the cycle Pantin was going to show carbon carbon double bond at roughly sixteen. Fifty and C S p to hybridized hydrogen apartment. Yes, Oh Spoto Iraq's carbon hydrogen bond. And so that's going to show between three thousand and thirty one fifty. Thie al Kind is obviously going to show the carbon carbon triple bond at twenty two fifty and the C S P H bond at thirty three hundred for be. The main difference in these molecules is that the first one, the carb oxalic acid, is going to have that O H. Bond. And remember in a car box Hill Gassid. It's hard to say exactly where that will show, but it will show above three thousand wave number. The second molecule for B does not have a no h bond in it, and so there should be no signal above three thousand, and so that makes that pretty straightforward to identify. Moving to C A C is also very straightforward. There should be the distinctive key tone signal in the first molecule at around seven hundred wave number. The second molecule and see should show carbon carbon double bond at about sixteen fifty two C S P to H bond again between three thousand and thirty one fifty. And the oh age bond on this O. H is not a carb oxalic acid as one and B wass. And so we know it should show between thirty, two hundred and thirty six hundred wave number, and it should be a nice broad peak for D. The second molecule and day has, ah, carbon double bonded to an oxygen. So again we should see that right around seventeen hundred on the first molecule, indeed, doesn't have a carbon double bounded to an oxygen. So again, that's very straightforward to identify. If we were given an I R. On knew that it had to be one of these two molecules, we could look right at seventeen hundred, and if there's a peek, it's the one on the right and If there's not a peak in seventeen hundred, it's the one on the left, so moving on e So when he this first al kind is symmetrical and so we're not going to see the carbon carbon triple bond signal because the molecule is symmetrical. But for the second molecule in a, we will see the carbon carbon triple bond. And so that should show at twenty two. Fifty in the C S. P. H bond should show it thirty three hundred for F again we're looking at you know how to distinguish these two molecules. And so the first molecule in F has a ness pee through. Pardon me. Jeez, The first molecule in F has an S p hybridized carbon bonded to a hydrogen which will show it thirty three hundred. And the second molecule in F does not have a nasty hybridized carbon down to ah ha Jin. So there will be no signal at thirty three hundred. And that's how you differentiate them on DH. This is, you know as faras experimental organic chemistry. This is one of the main uses of I R. If you know what you should have, what functional groups should be there. It's very straight for forward to look at an I R and see if the signals are where they're supposed to be. And so that's sort of what we use this for an industry, a lot of time. And so that is the answer to Chapter thirteen. Problem number four.

And only by day I asked. Patrol beats each of it. Good morning to you. The first one is 4 19. Too old or 19? 21 one toe, three food fight thinking too old. 1234 I never wanted. Yeah, so if you look at the structure, there is no conjugation and soul beginning. This is an issue. Later, kiddo. Go, which appears at 1715 centimeters. Universe, that is the key to speed. And we won't know adoption this place in my breast now feel everyone over the second car bodies to die middle. Yeah, or he has threes years. Everyone's here. She was here. That is three pending. Too old He thinking too old. Yeah, Here is contribution. So the least contribution on defeat. Off softened. Relax. One thing Age. What is significant votes? The third, um, movies who do die Emulate cycle Abendanon Cyclo Pinned it all to to die Mealtime. This is a prime number. Ring he don't Andi. It appears it so plain emerging. Appears at 17.2. Sending between words. Next, my tiger. Ruben. Guilty hired Windows blown off. Absorption. Uh huh. 170 Quite 170 play. You do see everyone for stretch and then 27 to 0 and 28 to 0 27 20 and to eat do hero absorption due to leave. See it publicly to look. Thank you. What we should we do this absorption? Next come moments like low. Have you? No one? You don't hear just three supplements, you know? So there is no congregation, so it will appeal at 17 One thing Significantly, Waas and the Mexican Bowl is uh yeah, okay to Hexen are to Cinar. 12345 Fix So 284 and everyone. So this is a communicated Tito a convicted and a Alfa Beta unsaturated Randy Haiti. So see, all absorption will be I had 170 plane for contributed idea heads.

So absorption is 824,720 suggests we have all the hide. 3000 absorption suggests we have hydrogen attached to SP three rods and SP to hybridize carbon. So therefore, from this analysis, we may determine to have two missile butor are behind which is drawn just below moving on to our second example here we have broadband at 3300 corresponding to an n H group. This is confirmed by the 1600 absorption. Secondly, there is an absorption at 1280 which is a me throw. Therefore we may have pro pro No a might present Well, we have that a might functional group moving on to our last example Here we have an absorption absence at 1600 meaning that there is no benzene ring. We don't have any meats are groups either are suggested by the absorption at 1380. Strong absorption at 1700 though, indicates the presence of a key tone. So our structure may in fact be set cloak Ito. Where are key tone is a carbon I'll that has to armed groups where neither off the ah group or protein protons on. We have six members Cyclical ring will the single bonds

This question, we are asked to figure out the structure off full compounds. Biggest done. Who? Animal spectra, given and metal that they all have the molecular formula C six its trail or so Because we see that there are two oxygen's present in this molecule formula. They could be from, ah esta molecules, carb oxalic acids, a molecule that has two separate Carbonell bonds. But let's just keep that information in mind by moving forward. And then if we take a good look at your first spectrum, they see that the most down face signal has integrated issue off to and because of the prisons off oxygen in this molecule, a farm lobby could predict that coming from a structure like this, and then we see that the next most down through signal is considerably over a from the first one. Um, with ended real issue off three, and we can account for that structure if we separated Oh methylene group and a metal group using the Ester group. And then we see that there are three mo signals corresponding toe integral ratios to toe entry, and, um, because they are spaced at similar distances away from each other. and the fact that there are two Oh methylene hydrogen possibly and Matile group. At the end, there's us that it is probably coming from long carbon chain that looks like this. And then if we take a look at those meetings to check the spectrum but the compound that we have our common to it, we see that the most on thin Cigna Oh, here. Oh, the growth down feel signal that should be coming from the methylene hydrogen is that I have so good Shouldn't be a triplet because of the proximity to to the other metal in high regions. I just undo it so to classman would be three and then the most up the signal coming from these hydrogen. It should also be our triplet because of the adjacent metal in group to that from all that exalted. And this is the structure goddess running do spectrum. If they knew woman through spectrum be you see that the most don't feel signora has an integrated ratio of one, so could be coming from a structure like this. And again you see that on there's a huge gap. It mean the most downfield signal and the next most on for your signal, which we could again account for using that structure like this and down. We have also accounted for the integral ratios. This has anti clear issue on, and this has the integral three. And then we see that there are three more signals a Manning, and they have integrations to three entry. So if they were pulled two and three and there was based or nicely with similar gaps from each other, we could say that it's probably from a linear carbon chain. But the fact that they are doing three signals there are two signals with three integrations. Um, then says that there are two metal groups, which means that it's not Arlena oh, carbon chain. And so it has to be something like this. And, uh, we stayed at dinner signal at 1.2 as a integral very few off. Three. It's a tablet, so it should be coming from these three hide regions that are connected to the carbon that has a single hard vision and then the most upfield signature. Um, coming from these three metal programs is a triplet. Because of their proximity to this Smith alien group revisions So this is the structure corresponding him to spectrum. Be many of them. We were born to spectrum. See, he you see that the most down thing signal has injected issue off to. So I could be coming from something like this. And then again, because of the distance to their next signal which has the integration off three, we could say that it is coming from structure like this and we see that there are two more weeks with integrations. Born in six, it could be coming from on material group that has to matter groups attached to it. It total off six hydrogen. So if we check with the respecting so we see that the most the whole field signal is a tower block. So should be coming from these hydrogen. And it is I just into a single hydrogen. So one blast bomb should be tablet and then the most often signal is also doublet. Andre should be coming from thes my little protons. And there I just sent you a single proton. So again they should. You guys stood up. So this is the compound corresponding. Just spectrum. See? Then it is no longer a spectre de we see that there are only two peaks and they are considerably close to each other, and they have integrations mile entry. This most probably comes from Courtenay Restructure like this because we have six governments to account for Oh, and have so few peaks. It should be coming from a structure like this. So here we have two dives off divisions run, and all of these are going to be equivalent Hydra agents and our mom. There's three of this and nine off the B type carbon, so the integral issues will be 123 and this should be the structure correspondent through Spectra D.


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