5

Propose structures for compounds that fit the following descriptions:(a) $mathrm{C}_{10} mathrm{H}_{14}$H NMR: $7.188$ (4 H, broad singlet); $2.70 delta(4 mathrm{H}...

Question

Propose structures for compounds that fit the following descriptions:(a) $mathrm{C}_{10} mathrm{H}_{14}$H NMR: $7.188$ (4 H, broad singlet); $2.70 delta(4 mathrm{H}$, quartet, $mathrm{J}=7 mathrm{~Hz}) ; 1.20 delta$ $(6 mathrm{H}$, triplet,$/ mathrm{m} 7 mathrm{~Hz})$IR: $745 mathrm{~cm}^{-1}$(b) $mathrm{C}_{10} mathrm{H}_{14}$(3 $mathrm{H}$, singlet): $1.20 mathrm{delta}(6 mathrm{H}$, doublet, $J=8 mathrm{~Hz}$ ) IR: $825 mathrm{~cm}^{-1}$

Propose structures for compounds that fit the following descriptions: (a) $mathrm{C}_{10} mathrm{H}_{14}$ H NMR: $7.188$ (4 H, broad singlet); $2.70 delta(4 mathrm{H}$, quartet, $mathrm{J}=7 mathrm{~Hz}) ; 1.20 delta$ $(6 mathrm{H}$, triplet,$/ mathrm{m} 7 mathrm{~Hz})$ IR: $745 mathrm{~cm}^{-1}$ (b) $mathrm{C}_{10} mathrm{H}_{14}$ (3 $mathrm{H}$, singlet): $1.20 mathrm{delta}(6 mathrm{H}$, doublet, $J=8 mathrm{~Hz}$ ) IR: $825 mathrm{~cm}^{-1}$



Answers

Propose a structure consistent with each set of data.
a. Compound $\textbf{A}$:
Molecular formula: C$_8$H$_{10}$O
IR absorption at 3150-2850 cm$^{-1}$
$^1$H NMR data: 1.4 (triplet, 3 H), 3.95 (quartet, 2 H), and 6.8-7.3 (multiplet, 5 H) ppm
b. Compound $\textbf{B}$:
Molecular formula: C$_9$H$_{10}$O$_2$
IR absorption at 1669 cm$^{-1}$
$^1$H NMR data: 2.5 (singlet, 3 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.9 (doublet, 2 H) ppm

This is the answer to Chapter 14. Problem number 65 Fromthe Smith Organic chemistry textbook. Ah, and this problem asks us to propose to structures. Ah, that are consistent with two sets of data that we've been given eso for each structure that we're supposed to propose. We've been given a molecular ion. Um, and I are spectrum in an enemy war spectrum. Okay? And so, starting with J, we're told that Jay has, um, its molecular ion at 72. Um and so from there, we can start to think about some formulas. S 06 carbons equal 72 s 05 carbons on 12 hydrogen ZX could get us to 72. Um, but I'm going to jump around a little bit. Ah, And in light of the fact that J has an i r. Peek at 17. 10 wave number, which is consistent with a carbon oxygen double bond, I'm going to say that there is anoxia gin in Jae. And so when I see the mtz at 72 I think this is going to be C four each aids. Oh, um and I think that because again, this I r tells me that there has to be a carbon oxygen double bond in here. Um, and so if the formula is see for H 80 the degrees of on saturation for that formula are going to be, uh, two times four plus two minus eight. All of that over too. And so that's going thio be one degree oven saturation on dhe. So I think this is, ah, the correct formula. And I think that we have a carbon oxygen double bond in this molecule s. So then we need to look at our anymore. Signals s 1.0 ppm. Triplet. That integrates to three. That's going to be a method group. Um, and I'm gonna skip the next signal on Look at this 2.4 ppm quartet that integrates to two. And that's gonna be a methylene group. Ah, And so these two groups are splitting each other. Uh, right, because we have a quartet on the methylene signal on, So that means it has three neighboring protons on the signal for the metal group split into a triple it, which means that it has to neighboring protons on. So these two are next to each other. They're splitting each other. Um, And then the last signal of the second signal here, the 2.1 ppm single it that integrates to three. Uh, that's going to be a method group with no neighboring Proton because it's a single it. Ah. And so if we put all of this information together, um, what we get looks like this. So here's our Carbonell. And then there's another method group on just to sort of spell this out S o. This signal is going to be this metal group. This signal is going to be this method group, and this signal is going to be this math linger. Okay, so there's, uh there's j and now we just need to do the exact same thing for Kay. So looking uk, we have ah molecular ions at 88. Um, and since looking at the i r for j proof so helpful, let's start with the i r. Here. So this time on the i r. Is a peak between 3200 and 3600 wave numbers. That's a broad peak. Ah, and so this is consistent with an O. H. So we have an alcohol in this molecule Um, And so again, we need to account for the presence of an oxygen. Ah, and so C five, um, case that 60. And then oxygen is gonna be 16. So that's 76. So let's go see five each. 12. Oh, okay. See? Five each 12 0 And so if we do the hydrogen deficiency index for that formula, what we get is two times five plus two minus 12 all of that over to equal zero. So there are no degrees of on saturation in this molecule us and no double bonds, no rings. Just a, uh, chain of carbons with an alcohol in it. Okay. Um, and so looking at our anymore the fourth signal, the 1.6 p p. M. Single it jumps out to me. This is probably, uh, the proton of our hijack see group. Um, Okay, So the 0.9 p p. M. Triplett are that integrates to three. Uh, that's going to be a method group. The next signal, the 1.2 p p. M. Single it that integrates to six is going to be to methyl groups. So there two metal groups in the same environment and they're not split by anything. Um, and so I'm gonna go ahead and guess that they are on our carbon with the alcohol on it. And then, lastly, we have 1.5 ppm. Quartet are that ingrates to two. So this is going to be a methylene group. And so again, notice we have We have a triplet are that integrates to three and a quartet that integrates to two. And so these two signals are splitting one another. Um, okay. And so when we put all of that together, we can put it together like this. Um, so let's do it like this, Okay? And I think actually, drawing it out with letters in this case maybe makes it a little easier to see. So obviously, uh, single for the O h. Eyes is this? Oh, age. Um, we have these two methyl groups that are equivalent. So that's gonna be these two method groups. Uh, and then we have, um, as I said, the methylene and the metal group that are splitting one another. Well, let's be consistent, I suppose. Oh, dear. There we go. Okay. So sorry. All right, so here we go. So this black arrow Obviously this is the methylene group, and then the blue arrow eyes referring to this method, Bert. And so this is a good structure for this molecule that fulfills all of the requirements that we were given on. And so that's the the answer for K. And then the answer again for J looked like this. Um and that's the answer to Chapter 14 problem number 65.

Problem number six. Okay, we are asked to propose structures. God, um, satisfy these requirements. Okay. So must go for it for part eight. Port A. You're given this, um, molecular formula C two h for Oh, right. And, um, they wanted to have another hide function group. Okay, so I want to draw that, starting with the all the height. So another Hyde would be hey, carbon with, um, a double bond with oxygen. So there's our carbon double bonded oxygen, and it has a hydrogen. Okay. And then all the hardest, always terminal. So I'm putting it at the end here, and, um, we have we have two carbons, and we already have one with all the hide, so we only need one more. Okay. And then we have four Hodgins. Me, I like that. You got four hundreds, and we have one from all the hide. So we're gonna need three more, Which is great, because this carbon could handle through more hydrogen escaped, so that should be our structure for party. Can't be. We need, um, this molecule to contain car book Cilic acid. Okay, so I want to start withdrawing the car book. Cilic acid So we have an old age group, right? We got the carbon double bonded to O. And there you go. Actually, maybe race this sport. Okay, so that's that's your car book. Selic acid. Right? And how many carbons? Two we need We need three. Okay, we'll go ahead and put two more carbons. We need three daughter, right? And then we have six hydrogen Sze about 600 Jin's okay, You already have one here, so we need to just add two more. Okay, so I'm gonna add that to our carbons, So me, but more space. Okay, so this, um second carbon could handle two more hydrogen and this last carbon could handle three more to make it four bonds cape so that, um that gives us a total of six Hydrogen tze and of course, those Those two oxygen's, um, are in our car book Selic acid. Okay, so moving on to part, See parts. He is asking for two ice Immers. Okay, so we're drawing two molecules here, and, um, they contain Esther groups. So, as usual, I want to start with the function group. Right. So I want to draw the base, um, based structure for Esther. So that should be your base structure for Esther. They're going to be a carbon on the left side and another carbon on the right. And we are drawing too, so I'll draw another one. Um, directly below it. Okay, so that should be our base structure for Esther. And we have four carbons, right? We'll worry about the hydrogen is later. We have four carbons, so I wanna maybe add one on the left and two on the right. Right. So that gives us four carbons. And then we have eight, eight hydrogen. So let's see if, um, we could fit eight just by adding into carbons. So this carbon Sorry, this carbon could handle three hydrogen sze. Right? Um this one could handle two. And the last carbon could handle three hydrogen tze and looks like it gives us a total of eight, which is what we need. Okay, so that's for our first I summer in her second I summer. Um Well, I put one on the left earlier, so maybe I'll put two on the left now. Okay, so I put two on the left and one on the right and let me fill out those hydrogen Sze actually just realized I need more space there. Okay, so this first carbon on the left can handle three more. And then this middle carbon could handle two more hydrogen and our terminal carbon here are last carbon could handle three and again, three plus three plus two gives us eight, um, hard digits. So those should be our, um, proposed structures for part C.

In this problem, I only fired by reading. It's objectively cities of reactions on the intermediates. How to bury identified it. The first step is C X day I So that should do. And c este si este place I am minus that should be are speech on treatment with medical wall. So what? I'll say the sponsor, the high court said I might. If you sleep by boy, it's minus until with them. Or it's minus this. Competed eliminates a more off water. We do it, you break the market off water. Forget it. That's everyone in the molecules. You know you. Yeah. So that is breakinmy If express so it is further Make it Make it the tsa ice that Yes, explaining. Tell Ammonium. Yeah. Come close, E. All right. I will again a reputation on the same cities of reaction Those Well, it's minus for X minus. Never. And plus Okay, we have sex. The photo. What? What? Always one is still absent from here. I they said they can even blue, resulting in the farmers now dying. Okay. Yeah, Plus it's tool. Plus trying me. Tell me this is the component. The municipal compost. This is the or its finances be. Hey, may I ask you so? That and the files all day. Indian wickets. Interaction. Okay.

The Capital X, Y and Z. That's been starting material and grieving. The product has already dividing from the reactions as well as the animal scrotum off. Then do it now. The reaction involved is there what, x he adds with the next year, if you like on my on treatment with today s four. This is he. Yeah. Uh, just look at this dog ambulance. We can expect your in direction of the sea and globe over here on the CME group. They refused to buy and they ended four. And you see it go. And it's true on job they have the that group. They are here, you know, Make it because the end of my food. So So it should be e galactic colleagues. Uh, company? No. Let's look at the On the morning of the gumbo, the animal shows a simulated one off to problems. Yeah, eight up one two x. Things like it's slightly broad. So possibly can be Niinisto Peak on. Then we have two signals that 2.8 and 2.9. When 7219 I'll play the same in the integration. Oh, for each each they're on. It's a multiple it there is a triplet. So this can be as here, too. On this will deflate to be That is also a that is also trip like, Oh, what are complex? So that means the beast. Welcome to you. Yeah. So now under 7.4 to 7.6 I don't like it on the integration is filing pro Bowls. So looking all this together, we can find the Z equals. See, It's juicy, it's cool. And it's too. Yeah, So this that's the one. This one I saw for 2.7. I don't know before nine. I possibly on business for the systematic global's. So why you should be the sign of compound So you still see it? Oh, and X oh, shouldn't really highlight. Yeah, which is? It can be, uh, Roman glory and etcetera. But the iron spectrum shows signals. H yes, they have. Uh, this is yes, but please. So in the he xto me up


Similar Solved Questions

5 answers
Hulu [ IWatchUU Bag [ Cosnclic FrdancerSkinETble Shows Somc Values Foronalreasoning netf/assessment{showteslphplaction snownexustareG4Y0 ursetf =McnSmuk OrllVHaleuca ArrouintNOL Madl (I)FacchcokThe graph of a functionshown below; and has E function inverse. Evaluate f "(3).0f-1(3) = ? 0 f-1(3) = 0 0f-'(3) = 1 Oj- ( = - 2 0f-'(3 =5Question of 26 Points possible: This aticminiContinue8
Hulu [ IWatch UU Bag [ Cosnclic FrdancerSkin ETble Shows Somc Values For onalreasoning netf/assessment{showteslphplaction snownexustare G4Y0 ursetf = McnSmuk Orll VHaleuca Arrouint NOL Madl (I) Facchcok The graph of a function shown below; and has E function inverse. Evaluate f "(3). 0f-1(3) = ...
5 answers
Suppose that the function f is defined, for all real numbers, as follows.X -3 if X < -2 f (x)= 4x+5 if X> -2Graph the function f Then determine whether or not the function is continuousIs the function continuous?Yes
Suppose that the function f is defined, for all real numbers, as follows. X -3 if X < -2 f (x)= 4x+5 if X> -2 Graph the function f Then determine whether or not the function is continuous Is the function continuous? Yes...
5 answers
Vathljl$Xy Yij Eaene TeinMoving to another question will = sve this resporQuestion_The Skewness ofX equals -Valid MissingMeanVanancc Ninmum Maxinum Mode125.013PercentilesMoving anotner question will save (nis rescons Type hereto search
Vat hljl$ Xy Yij Eaene Tein Moving to another question will = sve this respor Question_ The Skewness ofX equals - Valid Missing Mean Vanancc Ninmum Maxinum Mode 125.013 Percentiles Moving anotner question will save (nis rescons Type hereto search...
5 answers
D Submit Answor of neon at constant pressur [0 2 Retry 1 1 Group H WJW 1 of1d group valume temperature XL Gs occmpies ur (h liters, will volume of 4228.5 mL; If the
D Submit Answor of neon at constant pressur [0 2 Retry 1 1 Group H WJW 1 of1d group valume temperature XL Gs occmpies ur (h liters, will volume of 4228.5 mL; If the...
5 answers
Write equation E-kQIn[m with the experimental values _ differences between ihe theoretical ofk and m, What are the percent the and experimental values of k, the expQuents suulation accurate in and n? calculating the electric field according to Coulomb $ law?a Equation becomcs E00 diference in k90 diflerent in nw0 difference in m
Write equation E-kQIn[m with the experimental values _ differences between ihe theoretical ofk and m, What are the percent the and experimental values of k, the expQuents suulation accurate in and n? calculating the electric field according to Coulomb $ law?a Equation becomcs E 00 diference in k 90 ...
5 answers
QuESTION 2K Zem Fenfon [alanee 141,l37 , 61,231-Jsnd 441,2,3)*2 YnakthaLale &ithe drecanal danvarn> D4lnwtere 4-43k?0<? 04 5
QuESTION 2 K Zem Fenfon [alanee 141,l37 , 61,231-Jsnd 441,2,3)*2 YnakthaLale &ithe drecanal danvarn> D4lnwtere 4-43k? 0<? 04 5...
5 answers
Problam. ort Corade forowrng Galr-JomaMzprlur. | - E 'E;'E,'E,' & elerenaryKove GaMfeei @nctdina FrubJ
Problam. ort Corade forowrng Galr-Joma Mz prlur. | - E 'E;'E,'E,' & elerenary Kove GaMfeei @nctdina FrubJ...
5 answers
Find all critical numbers of the following function.f(x)= sqrt x / (x^2-1)
Find all critical numbers of the following function. f(x)= sqrt x / (x^2-1)...
5 answers
QUESTION 1Which of these is capable of scavenging and removing hydrogenperoxide in the cells?Glutathione peroxidaseCatalaseThioredoxinAll of theseThese are all inhibitors of respiratory complex IV of theelectron transport chain except;AzideCyanideRotenoneCarbon monoxide
QUESTION 1 Which of these is capable of scavenging and removing hydrogen peroxide in the cells? Glutathione peroxidase Catalase Thioredoxin All of these These are all inhibitors of respiratory complex IV of the electron transport chain except; Azide Cyanide Rotenone Carbon monoxide...
5 answers
6t and [BO)]=| find [IA()I[B6)]ds 4t2 . Given [A6)]= t2 +1
6t and [BO)]=| find [IA()I[B6)]ds 4t 2 . Given [A6)]= t2 +1...
5 answers
Sketch the graph of xy = and find the asymptotesand
Sketch the graph of xy = and find the asymptotes and...
5 answers
Ifr = r(s) is a position vector ofa point P on the curve €, and ifr" = K'n- K2t + Ktb then find r(v) and r(vi)_
Ifr = r(s) is a position vector ofa point P on the curve €, and ifr" = K'n- K2t + Ktb then find r(v) and r(vi)_...
5 answers
Identify the nuclcophilic site and thc clectrophilie site Ihc following rcaction Add cuned niows show Uhc movcmient of electrons Ihe tcuction step (2 pts)
Identify the nuclcophilic site and thc clectrophilie site Ihc following rcaction Add cuned niows show Uhc movcmient of electrons Ihe tcuction step (2 pts)...
5 answers
Flnd 8 DETAILS 1 1 LARATRMRP7 5.6.006. 1 8 Submissions Used Jumn1
Flnd 8 DETAILS 1 1 LARATRMRP7 5.6.006. 1 8 Submissions Used Jumn 1...

-- 0.066918--