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13C NMR Spectrum (100. MHZ, CDCI , solution)DEPT CHzl CH;t CHTsolventproton decoupled80406 (ppm)200160120expansionIH NMR Spectrum (400 MHz , CDCI , solution)7.65 7....

Question

13C NMR Spectrum (100. MHZ, CDCI , solution)DEPT CHzl CH;t CHTsolventproton decoupled80406 (ppm)200160120expansionIH NMR Spectrum (400 MHz , CDCI , solution)7.65 7.45 6.85 6.65 ppmTMS106 (ppm)

13C NMR Spectrum (100. MHZ, CDCI , solution) DEPT CHzl CH;t CHT solvent proton decoupled 80 40 6 (ppm) 200 160 120 expansion IH NMR Spectrum (400 MHz , CDCI , solution) 7.65 7.45 6.85 6.65 ppm TMS 10 6 (ppm)



Answers

Match the $^{13}$C NMR data to the appropriate structure.
Spectrum [1]: signals at 14, 22, 27, 34,181 ppm
Spectrum [2]: signals at 27, 39, 186 ppm
Spectrum [3]: signals at 22, 26, 43, 180 ppm

Hi, everyone. One age, the normal spectrum or being seen shores. Oh, sing leg I Hi Year Delta off some 0.2 ppm. Big because they're not because the benzene dream. Yeah, not only consist, stop consists off. Alternative single and double bonds, Single can and double box. Yeah, Trump, but unsold. It has a ring strain A ring strain. Do you do? Hey, exact journal. Close structure. Clothes struck Chip. On the other hand, on the other hand, Sunday Other hand 13 Butor dying Butor dying So although it is conjugated so those it is conjugated shots Lower frequency peak. Okay, free quinces. I Delta fire you comma the top 5.1 and 6.3 PM You hear? Since it has open structure open structure I am doing strain is absent on the ring strain is upset of sand, right? Secondly, aromatic compounds A I don't My big compound A shows mass spectrum pig spectrum peak. I am I said 104 Therefore the compound heads molecular formula. See a day agent check. Secondly, the 11 tell analysis off A unless it's off a indicates you know for example element the percentage then atomic ratio Dane Sim Blessed atomic ratio 11 days Carbon hydrogen 92.3 This is 7.7%. So this will come at the 7.69 This is 7.7 simplistic comic racial point people Line, this is one so whole numbers that is in tow Aid. Get eight toe eight again aid and therefore no their fault. The formula of the components the comm Bondi's combined aids C h h aid Angry restructure is structure off is as follows. So structure up Is this true? C h that we want ch two So this sort a compound a Now this component a combined a under rumination Yes. Cambone be Be so sure. Okay. C h double one ch teau less We are too. So this is basically sliding. So one robin is I didn't do this against the first Carbon and other women is ready to stake in carbon ain't will get well, kids ch br ch trupia. So this is what they compounded. Gate nineteen's one Bram Oh, one fan Ill. Yeah. Uh, we can greatly this also that this one to diagram Oh, on to die a brahma one final We think the thing So this is combined A and this is combined The okay

This question gets us to and in my spec job and met war that the two belonged to to carve oxalic acid but the same molecule a formula C three h five. Or to see it sort of me arrange the carbons in the back. Born. We have to have this diver structure for both of the car back to the passage. The three carbons would be along the backbone and the end with the carb actually group, which is the case for both of these. It struck just But let's try to arrange the rest of the atoms in a molecule a formula so that these card boxes, I guess it's been give rise to death. Oh, animal spectra drawn in front of them. So in the first kiss, we have a quiet it, which is downfield and on a tablet that is up here. So this spectra is ignoring the proton from this, um, car boxes group. It is going to be further down field in both cases, so we can really use that signal toe distinguish between these two because it's the same thing. The san case. We put up them, but let's look at the rest of the pigs, and they're called it that this donkeys years correspond to a proton are set off photons that is very close to, ah, chlorine atom and a descent to a metal group. So to fulfill those requirements, we can try the structure. I understand the, uh, in agreement with that with that part of the NMR spectrum. And if you look at the doublet, which is upfield, it has to be coming from a pro don off set of protons that top. I just don't do have carbon that has a single broke down. So they're only protons remaining in the structure is demented or don't And if we considered established to be corresponding to the metal protons, they have to be. I understand to a carbon that cast out sing that hydrogen. So let's revaluate refuges, said the Carter That is downfield corresponds to a pro down are a set of prudence that are very close to the clothing, and I descend to ah metal group. So that would be this hydrogen corresponding to this Kartik and then the doublet that is upfield is coming from a set of protons. That dog I just sent to a carbon that has fine hydrogen, which is the case for this method group. And it is significantly further away from the Electra Negative Florin. So it has a feel signal. So this structure fits that. Make this ending my spectra. Then if we move on to the second Spectra, it has to triplets, which can only mean that there are two methylene groups. I mean it at this. So there are two mcgillian groups and we have our own clothing left in the structures. So for want of them to be rattling groups, we have to have the clothing attached here. So now let's again check this spectrum bitter molecule that we just constructed. He has to have do met the lingo, dawns two sets of material in protons. So we have two sets of Medvedenko dance here, and then one of them would be downfield which says that it's connected to a clothing and that there will be upfield. Come back to that. So this spectra isn't a agreement with that structure. So in the first case, we have to chlor Oh, propane. I guess it that corresponds to the first spectra. And in the second case, we have three Chlor Oh, proper Nike ascent corresponding to the second Spectra


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