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1. Show below is the mass spectrum for propionic acid. Draw the molecular mass fragments that contribute significantly to m/z = 29, 45 & 74. In addition identi...

Question

1. Show below is the mass spectrum for propionic acid. Draw the molecular mass fragments that contribute significantly to m/z = 29, 45 & 74. In addition identify the base peak signal and molecular ion signal on the mass spectrum.10080[ L 4020t+t+++TTT 10 15 20 2530TttttH+ 35 40 45 50 m/z5560657075

1. Show below is the mass spectrum for propionic acid. Draw the molecular mass fragments that contribute significantly to m/z = 29, 45 & 74. In addition identify the base peak signal and molecular ion signal on the mass spectrum. 100 80 [ L 40 20 t+t+++TTT 10 15 20 25 30 TttttH+ 35 40 45 50 m/z 55 60 65 70 75



Answers

The mass spectrum for a compound with molecular weight of 102 is shown below. Its IR spectrum has a broad, strong absorption at $3600 \mathrm{cm}^{-1}$ and a medium absorption at $1360 \mathrm{cm}^{-1}$ a. Identify the compound. b. Show the mechanism for formation of the peak at $m / z=84$.

This is the answer to Chapter 12. Problem number four from the McMurray Organic chemistry textbook. This problem asks us to list the masses of the parent ion and of several fragments we might expect to find in the mass spectrum of the molecule that were given eso every drawn, that molecule. It's to metal to Penhall. Um and so we need to think about what types of fragmentation this molecule can undergo. But I guess the first thing that we should do is t count up. Um, all of the carbons hydrogen is and the oxygen in this molecule, um on Then use their am you values. So 12 for carbon, one for hydrogen, 16 for oxygen on. Add them all together. And that is going to tell us, Um, the mass of the parent I on here s of the M plus Peak is going to be 102. So we have six carbons, 14 hydrogen xenon, oxygen on. So when you do the math error, it adds up to 100 to, um okay, and then we need to think about possible fragmentation. Here s so this is an alcohol. That's the only functionality in this molecule. Um And so remember, from now this chapter of the textbook, that means that we can potentially see dehydration. Ah, and Alfa cleavage. And so, um, there are two possible Alfa cleavage pathways s so that the first pathway, which I will show in blue eyes gonna be this dehydration here. So the loss of water on and so how blue arrow that down. Then we can also get out for cleavage here, Uh, this carbon carbon bond or, um and probably more likely we could get Alfa Cleavage here at this carbon carbon bond. Okay, um, and so it's looked the Alfa cleavages first. Eso if we follow the red pathway if we break are the bond that I drew a line through in red What we would get, um, would be a methyl radical. So here's our radical. And remember, Since this isn't charged, we're not going to see it on the mass spectrum. Um, but what we will see is the rest of the molecule, since that's the charged fragment that is going to this. Okay, on this will you can't ions will have a positive charge there. Um, and the M two z for this fragment Eyes going the 87 to remember loss of a metal group, um, is loss of 15 atomic mass units. So our M plus people's +102 we've lost methyl group saw and two Z here is 87. Okay, um, the other alfa cleavage pathway that we can undergo. Ah, would be breaking the green bond there. Ah. And so when we break that, um, we're going to get a Pro Bowl radical. Um, again, there's no charge on this radical, so we're not actually going to see it. Um, And then the rest of the molecule, which we will see, I will look like this cake. And this is our cat eye on. Which is why it's the fragment that we see and the M two Z for this fragment. Eyes going to be 59. Okay. And then lastly, um, as I said, we can we can undergo Ah, dehydration. Ah. And so the product of that dehydration is going to this. Okay, um and so this, uh, will be the charge species here, Um, as well as being the radical, um, we'll also get water as the name dehydration implies. So we've lost water. I'm and in the MTZ for the charge. Species charged fragment eyes going to be 84 on and again. Remember that dehydration loss of water? Uh, you lose, um, 18 atomic mass units as a result of that. And so, with an M plus peak of +102 this fragment having lost 18 due to water, the MTZ will be 84. Okay. Ah, and that's the answer.

This is the answer to Chapter 13. Problem number 23 fromthe Smith Organic chemistry textbook. Um, and this problem gives us a ball and stick model, um, and tells us that the mass spectrum of this compound shows fragments at M to Z 1 27 1 13 and 85. I mean, we're asked to propose structures for the ions that give rise to these peaks. Um and so the way that I chose to approach this problem, I think it's a good approach. Is Thio out of all the carbons and hydrogen is here, um, and calculate what the molecular ion would be on. So in this case, the molecular ion is gonna be 142. I'm and then bear in mind that, uh, to remove a metal group that's gonna be worth 15 and to remove a methylene group is gonna be worth 14. And so the ions that were asked to account for our 1 27 and so 1 27 is 1 42 minus 15. So it's gonna be 1 42 minus a method group. Um, and then the next one is 1 13 and so 1 13 is gonna be 1 27 minus a methylene group. Ah, and then the next one that were asked to account for is 85. So let's see, 85. Um, so ah, we could do to methylene groups there. Right? So 1 13 minus 28 is gonna be 85 so it's gonna be too methylene groups. And so thinking of it that way, it becomes pretty straightforward to see, uh, exactly what we're talking about here. So I did. The peek at 1 27 is going to be due to cutting this bond. So we're gonna be cutting out, um, a method group there. The peak at 1 13 is going to be from cutting this bond or the other bond to the Ethel Group. Um, right, because that's gonna it's gonna be 29 1 42 minus 29 is gonna be our 1 13 and then to get to 85. Let's see, So they get to 85 we need to remove a metal group. Ah, and then three methylene groups. And so we have that here. So we could cut this bond here. Um, okay, so then all that we need to do is draw are the ions that we're going to get from cutting each of those bonds. So to get the 1 27 peak, So, um, the 1 27 peak is going to result, Uh, from this, so we'll have ch three ch two. So everything about this molecule is going to be the same, except we've cut at Metal Group. And so obviously, you could cut a metal group, You know, any anywhere There are four choices for methyl groups. Toe cleave off here, but I'm just going with the easiest one, the one that's attached to this sort of central carbon. It just makes the most sense, I think, to try to visualize it that way. Um, so there'll be a positive charge on this carbon, okay? And so that's the ion that's going to give rise to the peak at 1 27 So then, for the peak at 1 13 we could visualize that, like, like this. So here's our central carbon. This time this metal group is intact. Um, this effort group could be intact. This side chain could be intact. Um, but we've cut off that other ethnic group and so are plus charge is there now? Okay. And so lastly for the peak that corresponds to 85 um, we can have our two f groups intact. So there's our central carbon. There's our mental group. Here's our second Apple group. Um, but we've cleaved off the four carbon chain to the right, and so we get this, Um, And if you wanted to, you could you could go back and add up all the values for these carpets and hydrogen is and double check. I'm the day add up these weights, but I know that that they do, right, because I sort of approached it the other way. I did it by subtraction, Um, and so double check. You could do all all of the addition and just just be sure, but I don't think we need to, because this is correct. Um, but yes. So that's that's how I would approach this problem and a lot of these mass spec problems, especially when it's just an Al Kane. Just remember that a methylene is worth 14 and a metal group is worth 15. Um, and then see if you know your fragmentation peaks correspond to 14 or 15 or 28 or 29 off of, uh, you know, the molecular ion. And then, if so, that tells you what what number of carbons you're removing. And that's the answer to Chapter 13. Problem number 23.

So here we're looking at on my spectrum for to me file plantain It's C six h 14. I'm just drawn out a rough sketch for a reference here. And so fastly we're looking at the first peak that represents and plus on our must. Here is about 86. So our final peak on our spectrum represents. And plus Secondly, we're looking for the base peak where our base people have a mass of about 43. Next, we're looking at fragments. So we have masses of 71 57 43 on 29 on they have the molecular formula off C five, h 11 plus C four h nine plus C 3 87 plus and C two h five plus, respectively. So lastly, we're just looking at Why does the base peak have the mass that it does? And so the base peak is a peak that the carb catalon with the molecular weight of 43 as this is the most stable Kabul cart on and off fragmentation process

The company's see poor. It's eight bull, see poor its seat. Who you sure ir signal at 17 30? You know you're this is this corresponds to a C O stretching vibration so more rigorous Coming, he said. They're already heard or a Titone under. So I only do both movies. I really had a Tito there, but it's got Do, um, must be must values when it's with 24. It is a bill. Speak under the 2nd 29 Don't change to bigger responding to his little group. See, it's the and see it too. Media group. No, the possible start is which we can draw. You are see? It's three. See? It's too See it too. It's too C h o. He's the only hood on the other. One is the key toe. See? It's day. See it too suitable. Want all See, it's state know the difference in them are you know the more months of these companies to we go to 72 Poor government 48 plus 8 56 Bless. The 16 comes to 42. So if you look at this morning cure, we can't Ingelheim a cleverly rearrangement for this and my property. Rearrangement, Monty. More like your So let me right, Because I d It's here. This is the MK liberty we have. It's 1234 governments years. So that is shit. This bones, This is my property. It wants. Well, it's double Want less? It doesn't work you. So the total of this cell see, it's too. So that s working. Class 12 will pay. 6 27 28 plus 16. That is 44. So, department, Tripathi, encroachment. And that is the most. Here is the base. They speak so they're given spectacles. One through this. So the government securities. Yes, honey. Hey, you open up. So this morning, it's not possible. No, On here. You can see they 29 can be a spring by department of this. Yes, but okay.


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