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Establish method to measure caffeine in a new tea brand 2. Determine the formula represented by the spectra below:INFRARED SPECTRUML3000

Question:

Establish method to measure caffeine in a new tea brand 2. Determine the formula represented by the spectra below: INFRARED SPECTRUM L 3000 2000 Wavenumber (cm-1) 1000 MASS SPECTRUM 100 1 2 120 160 Mz


Answers

(a) How many signals would you expect to find in the $^{1} \mathrm{H} \mathrm{NMR}$ spectrum of caffeine? (b) What characteristic peaks would you expect to find in the IR spectrum of caffeine? (Check your book to see figure)

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Taking a look at some physical chemistry. So the first thing that we're doing here is calculating are reduced mass. So are reduced. Mass is 1.78 Multiply that by 78.918 and then divide that by 1.78 Add 78.918 That's an AM you we then multiply that by 1.66054 times 10 to the negative 27 kilograms for I am you. So we have a reduced mass value of 1.65 24 times 10 to the minus 27 kg.

So now we can use the equation for force of a spring to calculate the vibrational force constant. So our next equation that users are reduced mass figure that we need what we re arrange for K which is here. So because 1 kg as to the minus two is one and M minus one, force constant K becomes 411.7 Newtons per meter to the minus one.

So here we're trying to elucidate the structure of a compound given its Max spectrum and its infrared spectrum as well. So to start off, we were given to peaks on the I R. So if you just draw makeshift spectrum over here with the Y axis percent transmits and wave numbers, Yes, access, we were told at around 1006 100 there is a broad, high intensity peak seen over there. And then, uh, 1360. There is a medium intensity peak.

Yeah, it's just trying drugs. So something like that is how the young spectrum might look like. Okay, so, yeah, Now it's time to start assigning some functional groups. So, yes, you probably already know what's over here in this region. If we have a broad, high intensity absorption in around 3600 in this region, you just check your correlation chart.

You will see that, Yeah, this is characteristic of a hydroxyl group. So very safe to say that there's an alcohol that we're dealing with an alcohol and even just to prove it further, this, um, medium intensity peak here, uh, 1260 wave numbers is also characteristics of the carbon oxygen single on vibrations. So we have already identified one functional group. Yes, we are dealing with alcohol. So for sure, dealing with alcohol.

Nice. So now lets them see well, but all three can elucidate. So we were given the molecular weight from them. Aspect is being 102 Master church. Yes.

Okay, so now we're just gonna use, um, math, Thio count number of carbons. So we know that I'm hydroxyl is 17. Master charged units. It's really hydroxyl. So if we just take that out of the way, get that way we get Let's just grab our calculators.

Get 85 master charge left. Okay, so now to count carbons, What we're gonna do is we're gonna then divide that by 13, and yeah, this is called the rule of 13. It helps us, um, count carbons. So we know that the C h bond does have, um, a mask. The charge of 13.

So then if we divide, um, the remainder muscular rate from the 13, you should be ableto count carpets, and that came out to be around 6.5. So then we can say that we even have six or seven carbons. Okay, so let's try and draw out our structure to see if we can get this molecular weight 102 Okay, let's start off with six apartments. Okay, so you draw it like that and start off with the primary alcohol alcohol just, um, to start off. Let's Yeah, let's count its molecular weight.

So it's molecular weight will come out to being So it's it's Harbin's. So we have to do six times 12 and oxygen. I am just the oxygen hydrogen hydroxide. Those kind of 100 Jin's. There'd be 3579 11 and 13 13 hydrogen to the compound.

And yet I believe we do get out to 102 France from all for the molecular rate, which is nice Lever sort of started to Yeah, our structure. But we would also have this exact same molecular weight. Um, if it was Game one hooks in all versus to Huck's in all versus three Hexen all so we still have to figure out which of the three it could possibly be. So then now we really need to look at the mass Spectra Thio figure out where we should place the hydra zone. Okay, so just to review some from the mass spec we need Thio review Base peak And what that ISS So, um, you remember the base peak is the highest intensity signal in a mass spectra, and it comes from the stable ist fragment.

So that basically means that it will be the signal that has the highest relative abundance. That would be like 100. And it it's so abundant due to the fact that it's stable. So after we eat radiated our sample with whichever electrons organization denies electrons toe charge it, then whatever's on dinar sample fragment, whichever those would be the stable ists would be the base peak. So here, see, screen our base peak waas 45.

He asked the charge So then Okay, yes. So we just now need to assign some, you know, functionality to this. So yeah, and we're doing that we would be able thio, figure out the placement of this hydraulic soul so you can't stop here and just call it hexagonal, right? Mhm. Yeah, because we do know textile. You just join the whether it's 12 or three and if you want to figure out whether it's 12 or three.

Now, we just need to look at how hexagonal can fragment. Okay, So, um yeah, the most common ways for alcohol's to fragment is through something called offal Cleavage. And that's just basically where the alpha position on a flex in all, which is just the neighboring carbon carbon adjacent to it. Maybe he's another color. Yeah, it's just the neighboring.

Um, Carbon. So this guy right here, This is awful for this one. It's the awful for that one. Okay, so then if we just cleave the Alfa Bond or the bond adjacent to the awful I mean then and form an opportunity in my on, we get off the cleavage. So let's just do this and the simplest way possible.

Yeah, so here we have it. We have hexagonal one thanks and all. So the way this guy would, um, pregnant is to form a ox sodium ion were Get this one over here. Other a radical, this end radical, going that end. And basically what we form is we basically cleave this bond, um, the part with this long chain and we're left with, like, a radical of this chain.

So from the carbons four carbons through radical. And then here he gets the oxen in my own, which is just basically a double Lee bonded, um, positive oxygen. So don't worry too much about that, but here this is the fragment that will most likely cause base peak. However, if you count on this guy's, um, molecular weights, this is 31 has to charge, which is still, um, all in short of what we need to get the correct based peak of 45 master charge. So it's close, so we can say that.

Okay, maybe it's most likely than to axonal, which would leave off two carbons instead of just one. So let's just double check. So here we have Hexen all if we make it to hacks in all and form it over here and cleave this bond right there to form this structure. And don't worry too much about this mechanism. This is just extra if you want to know how we can elucidates which, um, the place my hydroxyl shit against life.

Mm hmm. And here now we can see that this as a master charge of 45 which is then proving that Okay, we are most definitely working with here, too. External. Perfect. So now, um, the part B was just asking for us to explain the peak at 84 Master charge.

Should have been block. Yeah. Okay, so right. So as he also would have seen the textbook. Another way for alcohol to fragment is through dehydration as a second sort of most likely fragmentation pathway.

So as it sounds like, we get the loss of basically like a water, okay, which Yeah, she's pretty intuitive as to what? Just so basically, we use the Hydra Axle as well as one of the hydrogen. The farm, like the elimination product. Yeah, but we get then it's just this all cane. I believe it is a radical. A radical cat ion.

Okay, they're So this is the peak there. So then, Okay. The way you can really recognize the dehydration, though, is that it would be the molecular ion pink minus 18, 18 small amounts for water. So then yes, just like that, it was 87 was pretty. It's a pretty nice give away the fact that we were going through dehydration pathway because our, um, like Either way, it is 100 to so then 102.

My 18 is 84. So then we knew for sure that it was most likely gonna be in the hydrogen pathway. So yes, the mechanism is simply watch of the hydroxyl as well as neighboring proton toe form protocol Cat ion of all King Illumination product. Okay, so let's we learned a lot today, so let's just review. Everything s okay.

First made a makeshift ir spectra demonstrating are displaying the two peaks that we've seen one of 13 60. And yes, these were clear giveaways of the presidents of hydroxyl alcohol in our molecule. Due to the spot intensity is very characteristic of alcohol. Okay, so we know we're working with alcohol. Then we did some math.

Give them the 102 unregulated. Wait. We subtracted the molecular weight of alcohol to see what was left 85. All right then, using rule of 13, we were able thio count carbons. So for six or seven All right, so then either have axonal or happen all so then start off external to church And yes, we got it is a Texan all.

But then Thio elucidate the placement of the hydroxy group. We looked at the base peak, which is the highest intensity signal caused by the stable ist fragment with 100 abundance. So, looking at the mass Spectra, we saw it to be 45 Massive charge. So, yes, if you look at the actually given there was this giant peak here, here, 45 that really gave us are based peak. Okay, so we know that the most common fragmentation thought for alcohol's is awful cleavage where the neighboring carbon bond is cleaved.

Okay, so this kind of mechanism here, this position here is Alpha. It's neighbor to a hydroxyl. And we basically cleave this volunteer toe form this radical component here and then the charged oxen IAM group here and, you know, mass spec on Lee. Um, the text charge species. So you don't see this, Really? But this is the one that we see, and but it did not have the correct master charge ratio.

So then if we placed it as a to hex, not we were able to use that same cleavage pattern to gain 45 masters ratio. So then we knew for sure. We were working with two checks and all That is the answer for parking, then for part B. Um, it was asking for what the structure is, what the mechanism was. Thio, get this kind of Ah, that's the charge ratio.

So if you just compare this number to the molecular formula that was given, we can see that it was It seems to be an M minus 18. And if you have an alcohol M minus 18, it is a clear giveaway off a dehydration profit away where his name says, we lose water hydroxy with another proton and we get an elimination product and so radical Cat ion all keen, okay?.

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.

Problem. 99 Caffeine. The stone land in coffee and tea has the molecular formula C eight, h 10 n. Four. Or to calculate the mass percentage of each element in the substance.

Give the answers to three significant figures. So this question is from Chapter three calculations with chemical formulas and equations. So the formula of caffeine is C eight h 10 unfold auto. So this is caffeine. So in order to find the mass percent of each element, we use the following formula.

So the mosque percent that is equal to massive component divide by total months of compound in 200 right? Okay. Or we can also right in this way. Also, most percent. That is a call to massive element in one mole of compound divide by total months of compound or Mueller mas of compound and multiplied by 100. All right, so now, in order to find the total mass of compound or the molar mass of the compound, So with the help of product able, we can find out the total months of compound So compound here is caffeine, and that is C eight, h 10 and for auto.

So with the help of product table. So in case of carbon, it is 12. In case of hydrogen, it is one in case of nitrogen. It is 14 and in case of oxygen, it is 16. So these are the exact values.

So So we get this 96 plus 10 plus 56 plus 32. So which we get this value is around 1 94. So 1 94 g is the total mass of the compound or 1 94 g per mole is the molar mass of the compound? Okay, so in order to find the percent of each element, so one by when we can see the mask percent of carbon. So as we can see that interests in caffeine eight carbon atoms are present, so eight multiplied by 12, we get 96. So then divide by 1 94 which is the molar mass of the compound or the total mass of the compound multiplied by 100 in order to calculate the percentage.

So on solving this we get the value of 49 point for it. So but we have to write in the three significant figures answers, so its value is 49.4 percent. Okay, so now for hydrogen. So similarly, we can find the mass percent of other element in case of hydrogen. So total 10 atoms of hydrogen are present in caffeine.

So one into 10 divided by 1 94 and 200. Okay, so on solving we get this value is 5.15%. So 5.15 percent most percent of hydrogen in caffeine. So now, in case of nitrogen, so must percent of nitrogen. So as a total, four nitrogen atoms are present in caffeine.

So for multiplied by 14. So we get 56 divide by 1 94 and 200. Okay, so on following this we get the value 28 point two 6%. So but we write in the significant three significant figures so approximately we can write. This value is around 28.9% Now, in case of oxygen, so same concept applies in case of oxygen also So most percent of oxygen that is equal to so total two oxygen atoms and caffeine.

So 16 multiplied by two. So which we get 32 divide by 1 94 multiplied by hundreds So we get this value 16 point for 9%. So with the three significant figure we get, this value is approximately 16.5%. Uh huh. So hence we can write finally, our answers.

Most percent of carbon than most percent of hi. A Trojan than mass percent of no Trojan. And finally, the mass percent of oxygen. Okay, so the most percent of carbon, it's 49.4. So that is 49.4% most percent of hydrogen.

That is 5.15% most percent of nitrogen, that is 28.9%. And finally, the mass percent of oxygen that is 16.5%. All right, so if we add all this percentage, so we get approximate value of 100%. So that means in caffeine. These are the most present of each element in the caffeine.

So thank you..

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