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Determine the structure of the compound having the molecular formula CoHsCly and this "JC NMR spectrum (just two signals): (12 points)antadz ral...

Question

Determine the structure of the compound having the molecular formula CoHsCly and this "JC NMR spectrum (just two signals): (12 points)antadz ral

Determine the structure of the compound having the molecular formula CoHsCly and this "JC NMR spectrum (just two signals): (12 points) antadz ral



Answers

Determine the structure of each of the following compounds based on its mass, IR, and 'H NMR spectra.

Hillary won. Today we're doing Chapter 19 problem eight, and this room asked to identify the structure of a compound with a molecular formula of C four. It's 802 and with each anymore, spectra of a triple it. That's your 0.9 at double its or multiply, representing two. Hydrogen is at 1.6 of triple representing, two agents at 2.3 and a single. It's representing 111.8. So how we should go about solving this is first we need to turn the degrees on saturation. So how we do that is, well, the degrees on saturation or the number of double bonds equals the number of carbons minus number of hydrogen and highlights over too. So it's eight or to my X number of nitrogen is over to. That's your over two plus one. So you're four minus four equals zero plus one equals once we one degree oven saturation. Sometimes you know we have one double bond in this molecule, and if you look at the beach and more data, we see that we have one proton that's going to be a single it so it's not neighboring anything that can ah couple or split the signal at 11.8. So right off the back, we can say that the only way that we can have a proton that is not neighboring any other protons is that if it is on this oxygen, that is next to a cardinal group. So essentially, we have a carbon so acid. So you know that this proton is extremely acidic, mean that is going to fall off very fast. And it's also highly de shielded by the left arm. A drying groups, uh, adjacent to it, one being this option one being the carbonnel auction. So we can say that because it's gonna be highly dif dif. You listen to be significant on the left side of special spectrum and have a high ppm value such as the one that says 11.8. So we know that this proton is gonna have the highest PPL PBM value. So we know that that proton is taken care of and now we have this one carbon here and this should be a second carbon here. And then let's draw the other two cartons to satisfy the molecular formula with straw straight chains and see if this is true. So let's now work on the most shielded proton. So we should have three protons here. They're going to be the most shielded furthest away from these electronic drawing groups. And these three protons are neighboring two protons here. So we should see triplets. Or we should see these three protons being represented by two plus one peaks that equals triplet for three peaks. So three proton should be representing three peaks that should have the lowest ppm value. And that's actually what we see. We see that a 0.95 ppm. We have three protons that correspond to a triplet. So now what about these two protons here? Well, their neighboring three protons All right, but they're also neighboring these two protons on the left. So these two protons and blue, these two protons and blue are gonna be represented by a multiplex. So remember, you have your n plus one times you're n plus one. So you're gonna have four times three is. You might have 12 peaks in this one maximal, and this should have an intermediate value of P p. M. Somewhere between the Black Protons summer between the green proton. So these blue protons, if you look in between. So we have 0.991 point 65 and 2.3. So we should be interested in 1.65 And in fact, yes. This indeed is a multi planet representing two protons. So this supports this potential structural we drew here. Now, what about the green protons on the left? There's no neighboring. Protons are right. There's two. So these two protons to be represented by a triplet and they should have the highest value compared to other than 11.8. And that's going to be actually 2.3 triplets representing two protons. And that's exactly what we see in our questions them. So this is the proposed structure with given the data from this question.

From the spectrum for The compound with C9 H 12, we can see that there is a signal around seven parts per million that would indicate an aromatic rain And it appears that it would integrate to about five hydrogen. So it's a mono substituted ring. So that accounts for six carbons and five hydrogen, Which leaves three carbons and seven hydrogen. There are three other hydrogen signals. We have a triplet, uh a triplet and in between a uh sex 10 of from splitting. So that would be the pattern for a proposal group. So the compound is propofol bending for the formula C five H 10 oh. We just have to signals a quartet and a triplet that are in a 2 to 3 ratio, respectively. So that's the tell tale sign of an ethyl group. And since we have five carbons and 10 hydrogen ins, we can accommodate two symmetrical ethyl groups, which would each group has two carbons and five hydrogen. So that would be Four carbons and 10 total if we have two ethyl groups. So that leaves one carbon and one oxygen left over. So the simplest way to accommodate that is to make a key tone that has ethyl groups on both sides of the carbon Neil. Then finally C nine H 10 two. Again, we have an aromatic signal in the 7-8 parts per million range. So we're going to have six carbons and five hydrogen is on the mono substituted aromatic rain. We have a quartet and a triplet in a 2-3 ratio. So it's going to be an ethyl group. The CH two part of the ethyl group is d shielded to four point um Past four ppm, About 4.2 or 4.3. So that means the uh That's CH two group has probably bonded to an oxygen and then we still have a carbon and an oxygen left over. So the easiest way to accommodate that is to construct an ester group where the carbon eel of the ester is bonded to the aromatic ring and the oxygen Alcock, see oxygen of the ester is bonded to the ethyl group. So that would be the structure of ethyl benzoate.

But this question We are asked to figure out the structure off a molecule that has the molecular formula C six h ken Oh, and gives rise to the following Ah, depth. The e p d dipped, say, 13 NMR spectrum. So they look at the depth spectrum. It will show us, um, the separate types of carbons present in this molecule. And according to that, we can tell that there is a single metric carbon. Did he with green carbons one medallion cover. And when we look at the old carbons region, you see that there is one under carbon that is not accounted for by any other region on BBC duct Mom carbon being positioned at 200 bpm or near 200 ppm. So a signal near 200 bpm usually comes from carbon hill carpet in a C 13 NMR spectrum. So we have on carbon in a group. Ruefly, take a closer look at the chemical shifts off these different carbons. We see that the mental garbine is really upfield, so it has to be far away from anything a little negative but double bond, etcetera under methylene carbons. Out of the three of them Bonnie's really downfield and the other two are considerably upfield. So the downfield Matile in could be coming from ch two doctors in world in a double bon and, uh, meaning the ch carbons. The medallion carbons. It is for further down still than the McMillian carbon also. Yeah, well, this could really be coming from the carbon that is on the other side of the double bond. And it should also be you said to that oxygen that is present in this molecule. So if we combined this information, we can come up with the structure like this because we know there's a carbon in group and the Met Thein Carbon has a really down for you signal. It should be close to the carbon group. That's it, I just said. And then we will have doing a McLean carbons. That's because going for like this. Well, then now methods comment. Sarah, this structure can actually account for only chemical shifts and the different carbons present in this spectrum. So this spectrum has a daughter, loved 123456 carbons under 3456 and then are in her decisions till three, 456789 10. And there's a single oxygen when we have accounted, Father. Oh, molecule that this shown in the depths spectrum.

This question asks us to identify the structure off, but come bound that has a molecular formula C eight inch pan. Oh, we're given the IR spectrum for this molecule and the proton NMR spectra for this molecule which we can use to interpret the structure. So if you look at the ir spectra, we see that that is no carbon is stretch Neil 1700. They have numbers. So from that we can tell that this compound doesn't have a Carbonell group. If you go back to the proton NMR spectra, we can see that there Oh, to double its near seven bpm. So pigs knee and seven ppm, usually called response to protons coming from the Benz ending. And, uh, usually we can account for each proton made a Benz injuring if there are no substituted groups. But we see that from the integrations. After two picks near 70 p and we can only account for two plus 24 benzene peaks, the stairs are stacked out of the six protons in a Benz ending, probably to off them have bean substituted. And so there are only 40 minutes and you see how all right how symmetric the do that Blood near seven ppm look. So that factors as that the bends ending in substituted to give it some symmetry. So there are two, uh, there are likely to substituted groups, and they are substituted in a way that will give some symmetry to the molecule. And then if we go to the, uh, upfield any off the NMR spectrum, we see that there are two peaks which are good, single it's and they each correspond to up, integrated to integration off three. So these two can. These two peaks can be coming from two metal groups and the fact that they are single it they're says that they don't have any adjacent protons, uh, on their carbon next to them. And after that, you see that line after single? It's out of the two single. It's in the up billion year off the proton NMR. Spectra up is is downfield. So there's a big neo people in eight ppm so that it's much more down field. Come back to the big Nia to find three bpm. So we have a Electra negative act, um, in this molecule of formula, which is oxygen and no oh, that that could be, uh, oxygen near one of these metal groups, which is making it give a really downfield chemical shift. So far, we have put together some information. There has to be a Benz injuring that has so substituted groups in a symmetrical So that is most likely a I mind for substituted men's in group. This is Bond and the stool three. Well, so that's most likely are 14 substituted benzene and then we have do omit their groups. Outcast Mitt I'm is actually be possibly really close to an oxygen and their boot, not just in two carbons that have hydrogen attached to them. If we give these, uh, these things in mind again with them together and construct destructive So this is the molecule that death, uh, ir spectrum at Leicester Proton NMR, spectra correspond to making call it one Madox e four methyl benzene


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