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A bottle is labckcd only "Compound B (CH,z) and contains colorless liquid. You have &xcn called in &5 an cxpent @ identify this compound from its spect...

Question

A bottle is labckcd only "Compound B (CH,z) and contains colorless liquid. You have &xcn called in &5 an cxpent @ identify this compound from its spectra:IR: 3080. 1646. 888 cm'HNMRchemical shift; Hz 1500 1200 900240021001800600300J=6.9HzJ-6.9Hz 13730compound B (CoHiz)6721

A bottle is labckcd only "Compound B (CH,z) and contains colorless liquid. You have &xcn called in &5 an cxpent @ identify this compound from its spectra: IR: 3080. 1646. 888 cm 'HNMR chemical shift; Hz 1500 1200 900 2400 2100 1800 600 300 J=6.9Hz J-6.9Hz 13730 compound B (CoHiz) 6721



Answers

An unknown compound $\textbf{A}$ (molecular formula C$_7$H$_{14}$O) was treated with NaBH$_4$ in CH$_3$OH to form compound $\textbf{B}$ (molecular formula C$_7$H$_{16}$O). Compound $\textbf{A}$ has a strong absorption in its IR spectrum at 1716 cm$^{-1}$. Compound $\textbf{B}$ has a strong absorption in its IR spectrum at 3600-3200 cm$^{-1}$. The $^1$H NMA spectra of $\textbf{A}$ and $\textbf{B}$ are given. What are the structures of $\textbf{A}$ and $\textbf{B}$?

In this question well, given a molecule formula and ir spectrum, and brought on in the more spectrum for each question and asked to determine the structure that corresponds to now that set of data. So we have four molecules to do this fit in the first time. The door has a molecule formula C five each dress. Oh, and when we take a look at the IR spectrum, we see that it doesn't have a common here peak at 1700 on your 1800 big numbers. But what we see that it has is, ah, see singer burned old diaper a group. So let's just keep that in my hand and then wonder. The NMR spectrum and the animal are spectrum shows us that that are five beaks, and if we somewhat the integrations for these peaks we get there are 12 so two plus trees fight and then the seven in the field area. So it's 12 altogether, and that is the number of Friday. Jin's We are good is present in this molecule overload, so we can consider the integration to directly correspond to the number of protons that is giving rise to each signal. Who any each kits. So once we figured out that we can also say that the really downfield signals ah kind of overlapped on each other and one of them has, ah, integration to buy. The other has integration three and there are generally downfield from there are you would expect met the lane groups and met their groups to be so that is a group on a atom that can contribute to this day shielded nature off Medellin on the metal group. And, uh, it would give rise to a structure like this that there's a mcgillian group on one end a na oxygen in the middle and amid their group, and I didn't So this, uh, the Medellin hydrogen, it's on the middle. Red regions will have billion here chemical ships because they have very similar environments surrounding oxygen. And, ah, since this ended with the middle group, that is the end off the molecule on that side. But we can extend the molecule, uh, past the ch Dooku. So we see that in the operation have to spectrum. There are three signals. Uh, but there are two hydrogen each and, uh, signal with three hydrogen is so those are most probably coming from two meddling groups and a single metal group. But the fact that they're nicely spread out across the region does us that it's most likely coming from a long chain off three carbons. So that would look like this to search your groups. And then that's the edge to regroup. So we have accounted for five carbons. Total of hydrogen is and a single oxygen, and he can see the triplet nia 0.9 BBM that corresponds to an integration issue. Three. And it's coming from the metal protons here. There are just into this metal in proton. So to class man is going to be three. And this fights ah, split into a triplet. So this is the structure corresponding to the first. A question in the second part of the question. If we take a good look at the IR spectrum, we see that it has a carbon instruction and that it also has a Seizinger Bondo type of structure and the door lead. It has a a molecule formula C six, h 12 or do so these two groups could be coming from a nester group or are they could be coming from a separate carbon in Lana CEO also. So let's take a look at the NMR spectrum to figure out the rest of the information. So we see that it has only two bigs on the total integration. Some would be one plus 34 but we have, ah, 12 hydrogen still account for the drill divided by four is equal to three, Which just ask that that that is, um, like there are three entities in, in case of in the case of each peak, each big corresponds to three entities that are unique, um, and equivalent to each other. In the case of the are the signal also signal that has an integral issue off month that has to be three ended days, that guy equivalent to each other that this giving nice to that signal in the months they have figured out that, um, we can also see that there's a big separation between the two peaks in this NMR spectrum, which tells us that one of them is really Electra negative. I'm sorry it is really close to Elektra. Negative species by the other is considerably, um, further away from the election of the 50 shielding components. So if we had to account for three times three with the big at around 1.2 ppm, the most likely structure they can come up is come up with this arc. Ordinary carbon that has three equivalent mental group attached to it and then could be used to be considerably upfield. We have do not have ah Electra negative group immediately close to it. But it has a carbon news burned men. There's also an oxygen that gives rise to the Ester group. And then there's the CH three, the chest, the three hide regions. But I equivalent to each other and give rice studio, um downfield speak with the integration of on. So we see that the premature groups have 900 Jin's and there Single Mother group has three hydrogen, so they reduced ratio would be 123 And that's the ratio that we're seeing from the NMR spectrum. So we have also accounted for all the atoms present that are from carbons in the court in every part of the molecule 56 and then 12 hard provision altogether and to oxygen. So we have accounted for, um, all the atoms and we can also see that the metal groups don't have ah, neighboring hydrogen attached on the carbon on the coordinated carbon. So they are going to give us a single it and the stream at the roots. Also not. I just don't do any neighbor that has hydrogen attaching them, so they will also give rise to a single it. And then if they move on to the good part of the question, the IR spectrum show was a carbon your group and, um, from the molecule formulas that last ir spectrum. We can tell that Dan is a carbon clothing type front, and we also see that Danny's of Carbon Single Bond or my mind. So if you move on to the animal spectrum, we see our three signals with the daughter into girl integration off one blustery blustery, which is seven. And that is the number off protons that we need to account for. So each integration, uh, can we directly correlated to the number of protons that is giving nice to that signal? So we see that the most downfield signal is coming from a single proton. So has to be coming, most likely from like a Metin group. And then we see that it is split into a cart. It which tells us that it has to be Pagis Unwto, a metal group that has three protons. So three plus run is full. Then we'll give rise to the corner and then they also see the up field agent off the spectra. Um and, uh, there we have a single beak. It's looks like a single it. Too bad they haven't given us his wounding version. But the door that Hey, guys, Indigo tissue off three. And then there's another big that has integral issue off three, but it is considerably downfield. So for this method, I grow dawn to be down Fear most like you to reconnect the door. Electra Negative group. In this case, it's morbid clothing. And then we also know that, uh, this molecule could have a It's the group because we have a C or single bond and incompetent. So if we go with the Esther Group, we see that one of the metal groups are really downfield. So the Esther Oxygen has to be facing that method group. So they're material that is upfield would be this and the material that is downfield is this and the myth dine that this don filled is this and you do the attachment to the clothing and the proximity to the carbon, your group the mid line would be nor extra down food. So this is the structure that corresponds to, um that molecule and are we see that the upfield Matile should give rise to Ah, single it and the downfield MacDill should technically be are doublet because it's a dash of this, but, uh, the NMR spectrum is not really clear, so we don't have a zoomed in picture and contrary, Dennis, it's a double Doris England. So it could very well be a doublet. I am sure this is the structure that corresponds to that information. And if they move on to the next part of the question, we see that the I. R s picture has a really broad peak at 3000 with numbers, and that usually corresponds to and ah, which warned. And ah, that is a carbon hill bond, which we can tell from the big near 1700 numbers. And the molecule of formula for the structure is C four. It's strange or two, and then you could be Ah, take a look at the I asked victim again. There's something I missed. Um, so that is a peak in the actually, you know that I don't think we can say that there's a big in the, uh, 1,202,000 region because it's so small. Julia, I don't think this has a siobahn enemy. And then if we wanted the brought on NMR spectrum, we see that it has a peak at Dan BBM. So there's a big that really upfield, and the toll that it has offset off two ppm and it's drawing near eight pp and PSOE it blasted will begin so that we should actually Binya can't BBM in its um but he have to, uh, mentioned that there's not enough for him to draw the entire spectrum using the scale. And so they had to, um, putting up smaller picture with the offset mentioned on it. So, um, that big usually comes from carb oxalic acid. So in the marsh spectrum joins us that there's most likely a carb obsolete Cassity. And then if we look at the operation off the NMR spectrum, we see that there are spread out creeks and this three of them, which usually does. I said, There's a long chain carbon, um, long carbon chains. I'm sorry. There's a long carbon chain within this kiss. Uh, three comments because there are three signals and outfield, eight year. So if we put all that information to get there, he has to be something like this. So we see that the metal protons would be the host upfield, and th do is closer to the car box suggested And the Carbonell grope. So it would be more down field and this ch do, which is closest to the car box. It would be the most outfield. And are we have the hydrogen that has a chemical shift. Nia 10 get'em with the carb oxalic group and the integrations also match 32 to 2 and then mine. But then BBM and then we see that the split ings also match. They're, um the peak at my V. P. M, which is coming from the metal group, has split into a chip. Let so it has to be. I just sent two protons and then them peak at 1.7 ppm is a mighty plate, so it has to be, uh, gave us 22 types of protons on the two sides. It is the case for these metal products metal. Ian broadens. I'm sorry. And then the this metal mcgillian brought Don, it would be the most downfield and it good speaking to us triplet, which is reckless. E assess the most downfield signaled here besides, the be at then bpm. Okay, so, yeah, we have accounted for their information available in the NMR spectrum and become the number off atoms here for goblins. And, um eight, eight hydrogen So three plus minus four thru window. Yeah, A traditions and to oxygen's. So yeah, this is also well in agreement with the molecule formula did that they have.

In the example here we're looking at Mass spec, followed by I R. So we are provided with a spectrum that has mustered charge ratio peaks on. We will determine the structure of our compound, so the greater the master charge ratio tends to be the base peak. This is the parent peak. So let's figure out the formula. So we have 100. Divide by 13 gives us six with six left over. So from this calculation, we determine we have six carbons, 12 hydrogen. This gives is a formula off C six h 12. Don't worry if you don't catch everything. I'm saying all of my calculations on the screens. So now, looking at our infrared, we have a peak in about 602,500 so this could represent our double bond. So using the information above, we can determine that the structure is trans to hack scene so we can draw this below. We need to have six carbons on, then on the second carbon, we have a double bond

This question were given a molecule, a formula and a seated in NMR spectrum to deduce the structure off different molecules so depressed in particular, the door has a molecular formula, the 11 edge 22 well, and then it also has a peak in the 200 region in its stated in animal spectrum. So there's a peak at toward 10 ppm, so this usually corresponds to her carbon in a carpet. So we contend that this molecule has a carbonated group. And then if we look at the rest of the NMR spectrum, we see the dead up five signals I did in the carbon a signal. But since we've accounted for the Carbonell carbon so far, this molecule having 11 carbon started, we still need to Akon for 10 min carpets. But if you look at the spectrum, be on the C five signals more other than the carbon cigna. So if we have to account for Ken carbons using five signals, it doesnt says that there are equivalent powers of protons in the structure and they also see that the carbon signals are distributed in a wide range. Uh, like in, uh, we can small distance distances from each other, and that is usually characteristic offer long chain carbon, that is, um, connected to a Electra negative group at one end. So the common I just sent to them have Oh, hi. Oh, and higher, um, density of electrons around them. So putting all the information together, we can conclude that this structure is most probably from molecule that looks like this has a carbon ill in the center, and then five Paris off equivalent. Cartman's you hear? These governs our equivalent age. I didn't these two, like over three Children. And sure this is how we will have a spectrum it. Six. Cigna's for such a molecule of formula, but you know want to do next. Part of the question. The molecular formula corresponding to the next question is C eight pitch nine br. If he isn't how a molecule formula there, the number off carbons and the number Friday Jin's are very close to each other and up over six, especially for the number of carbons there's most likely of benzene ring in the structure. And if we look at the see that in an immersed picture, obviously that that out beaks in the confident in 270 ppm region. So this also tells the same thing. Both of these information tells us that Daddy's out Benzene ring in this structure. So if you accounted for benzene ring, we have accounted for six carbon sofa. But this structure has eight carbon, so they have to more carbons your come from and grew mean at them to come from. So we look at the benzene signals. You see that there are four of them and, ah, do off them have higher signals and now they do have smaller sickness. So this is usually characteristic off. Um, Ben's in carbons that have substituted groups in them. So the two signals that are mountains would have, uh, more carbons corresponding to those signals as well as hydrogen is attached to them. And the two carbons that have smaller signals would have a lower number of carbons. And then there'll be less equivalent carbons in them, as I last most likely carbons that don't have hard regions attached with. So by that logic, if we need to have four types of carbons and benzene ring, the most likely need to have a doubly substituted or benzene ring with the violin for positions substituted. And if we again go back and look at the upfield area after in the most victim, we see that there are crew Cygnus there and they are in the range. Bardo make their and Medellin carbon. And because the signals for these metal and metal in carbons are in their usual range and now, uh, not down treated come back to where they should be. We can tell that the broom in is not attached to either of those carbons. So one of the substituted groups has to be a booming. And since they have Rometty, Lennar matillion the meaning, most likely they will be coming from. And at this group, that is a dashed with it tradition that we have benzene that has a booming attached to mom position, and, uh, at their groups substituted to their full position. That's the structure this information corresponds to next. If they wanted the next part of the question, we see that the molecule of formula that our corresponds to our structure of it. Six carbons, 10 hydrogen is and more knocks it so again, he every have and garbage and to win minus two hydrogen. So if they had, uh, only saturated bonds, we would have to win plus two hydrogen. But, um, because we have two in minus stool, this corresponds to two on situations in this structure. Let's just keep that in mind and be called back to the structure of you See that does it signal at 200 plays BPM so that signature is us that has to be a carbonate group in the structures. And then, if we look at the axillary gently c three. Cigna's corresponding to three types of carbons, but the molecular formula has six carbons, so they have to be equivalent carbons in the structure. So because there are to warn situations in this structure, it couldn't most likely correspond to her psychic carbon Jen. So if they had a carbon in a group on one of those Karpin's and hydrogen have you got does you have a structure of it? One unique carbon there to we could learn drawdowns. I'm sorry to equipment and carbons. Get in here to recover and carbons here in here and not a unique carbon over there. So we have four types of carbons, this structure and me to look at the spectrum. We have four sickness. So that is the molecule that corresponds to that information. Then let's move on, kiddo. Final inspection and not corresponds to a molecule. A formula C six, it's trip. So again we have. See in it, do it type. You ever see an edge to and type molecule formula? Which does is that there is a single on saturation in this, um, compound. And then we see that that is a signal that is really downfield compacted out the signals. And this is in the age for her. I call it a carbon. Oh, I'm just at a keen carpets like the cop in that has a double bond. Not that street. And then Lee have six carbons in the structure, but we only have three sickness. So again, letters, I said they're up equivalent tears off protons and said it could have a grueling gas of carbons in the structure. So if we have a single double born in the structure and we have equivalent carbons, that double bond has to be in the center and then tohave Truman, um, carbon types, you should have a structure like this. So here we have thes carbons that are equivalent each other. And then these governments equivalent reserve them. This So this will give rise to three singles and there signal corresponding to the A dive. Carbon will be really downfield because they are connected to our Jeanne. Oh, carbons. It's the dough covers. So that's the structure that this molecule a formal up They're correspondent.

Formula C eight H 10 0. Can only be an alcohol ether. Alga Haider Key town. We can tell from the IR spectrum that there is no hydroxy group. I know carbonell group. So that leaves us with in either the proton NMR spectrum shows a double to double its in the aromatic region, which indicates a paradise substituted benzene. And then there are two single it's that both integrate 2, 3. So that means methyl groups that have no neighboring hydrogen. One of the methyl groups is D shielded to the neighborhood of four parts per million. So that indicates it's bonded to an oxygen. The other method group has shifted to two something parts per million, so that indicates that it's bonded to perhaps an sp two carbon. So we can draw a paradise substituted reign with him at Foxy group on one end and a methyl group at the opposite end of the rain. That gives us a carbons 10 hydrogen and one oxygen, which is consistent with both ir and NMR spectra.


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