Chemistry Quiz on empirical and molecular formula

AI Thread Summary
The discussion revolves around determining the molecular formula of an unknown organic compound based on combustion analysis, which produced 35.2 g of carbon dioxide and 18.0 g of water. Participants analyze the ratios of carbon and hydrogen derived from the combustion products, leading to confusion regarding the presence of oxygen in the compound. They highlight that while all carbon and hydrogen in the products must come from the compound, the oxygen in carbon dioxide and water cannot be solely attributed to it. The conversation emphasizes the need to consider the molecular weight and the possibility of additional elements, such as nitrogen, in solving the problem. Ultimately, the participants express frustration over the lack of sufficient information to definitively determine the compound's formula.
  • #51
ghostanime2001 said:
searching for a compound with fewer than 8 carbons seems like painful work. There are thousands of organic compounds and several compounds could have similar molar mass. I don't think this question was meant to be more confusing than it's meant to be.

Right now we are trying to establish a molecular formula, the numbers of atoms in the molecule, on the basis of information we have. This is really quite easy, certainly the next step. There are not thousands of numbers less than 7, there are only 7 of them! You know the ratio of H atoms to C atoms. On that basis what number of C atoms are possible?

Frankly after you get that you'll kick yourself. I think you'll do well then to ask yourself what was stopping you get it, it may be useful to you since you seem to be voluntarily going through old papers for revision or something. I would be interested to understand myself.

So try and answer the above question. If having tried you still can't say anything about that come back for more hints.
 
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  • #52
I know the reduced ratio of C:H is 2:5 from 8:20 ratio but I don't undestand what you said there about something having only 7 compounds with the above mentioned ratio.. to be quite honest, I don't really know if this question was meant to be this complicated. I guess I do need some more hints.
 
  • #53
ghostanime2001 said:
I know the reduced ratio of C:H is 2:5 from 8:20 ratio but I don't undestand what you said there about something having only 7 compounds with the above mentioned ratio.. to be quite honest, I don't really know if this question was meant to be this complicated. I guess I do need some more hints.

I said essentially, several times now, the compound can have only 7, 6, 5, 4, 3, 2 or 1 C atoms.

Which of those are commpatible with your 2:5 C:H ratio?
 
  • #54
2 carbon compound ?
 
  • #55
ghostanime2001 said:
2 carbon compound ?

Yes, that appears compatible. Why? Are any others compatible? Which are incompatible?
 
  • #56
Any others would not be compatible because the molecular formula is a integer multiple of empirical formula ?
 
  • #57
ghostanime2001 said:
Any others would not be compatible because the molecular formula is a integer multiple of empirical formula ?

A true statement but I don't see any logic as an answer. But maybe we can do it this way.

What is the empirical formula of this compound? I mean just the C and H part of it.
 
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  • #58
empirical formula = C2H5
 
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  • #59
ghostanime2001 said:
empirical formula was C2H5

What then are possible molecular formulae in our case?
 
  • #60
The possible molecular formulas may be:

1. C4H10 n=2
2. C6H15 n=3
3. C8H20 n=4
 
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  • #61
ghostanime2001 said:
C4H10, C6H15

so C4H10 seems to be the most probable compound

Do you have a reason for saying that?
 
  • #62
C4H10 has the correct maximum number of hydrogens, 2n+2
 
  • #63
ghostanime2001 said:
C4H10 has the correct maximum number of hydrogens, 2n+2

That is rather dodgy. Something like that might be true if this were an alkane, but don't we already know the compound is not C4H10 and there must also be some other kind of atom there?

So for the moment the only possibilities are C2H5, C4H10 and C6H15.

Now suppose we think there is only one other type of atom there, oxygen. Can you see how to go about finding what number of O atoms there could be in the above three cases?
 
  • #64
Why do you say
but don't we already know the compound is not C4H10

get the total number of oxygen atoms from CO2 and H2O then multiply that by 2 or 3 (molecular formula integer multiple in C4H10 and C6H15)
 
  • #65
ghostanime2001 said:
Why do you say

get the total number of oxygen atoms from CO2 and H2O then multiply that by 2 or 3 (molecular formula integer multiple in C4H10 and C6H15)

We've already said we do not know where these O atoms come from. Whatever number there are in the compound won't affect how much CO2 and H2O we get, which will just depend on the C and H.

Another hint. A key in school chemistry (and math) and not just school is "use all the information you are given". Usually questions see to it you have just the information you need (real life problems are not so easy and you have to know yourself what you need). But I have to keep reminding you of information (little) you were given! Refer to #1 again.
 
  • #66
let me just ask, do you already know the answer ? I have re-read post #1 and I still don't know other information missing. We won't get into the matter of oxygen in the compound, as you've already established that. How would I know there exists another unknown element without knowing the mass of the unknown compound. I have used all the information I'm given, I don't see any other information that I have missed. Maybe it said only "carbon-hydrogen analyzer" so I assume there is carbon and hydrogen ONLY ? Maybe I need to assume 100 g of the compound so I can determine mass percent ? .. since mass percentage remain the same regardless of the amount of the compound. I think you mean something like this maybe? http://chemwiki.ucdavis.edu/Analyti...ve_Analysis/Virtual:_Carbon_Hydrogen_Analysis
 
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  • #67
ghostanime2001 said:
let me just ask, do you already know the answer ? I have read it over 3 times and I still do not know what other information I'm missing. We won't get into the matter of oxygen in the compound, as you've already established that. How would I know there exists another unknown element without knowing the mass of the unknown compound. I have used all the information I'm given, I don't see any other information that I have missed. Maybe it said only "carbon-hydrogen analyzer" so I assume there is carbon and hydrogen ONLY ?

We've already been through that! With only C and H you got C8H20 - this fits the molar mass but you realized it was chemically impossible. So we conclude it must be from a smaller molecule with the given C/H ratios, and have now narrowed the possibilities to three. But with the numbers of C and H atoms in those cases we don't make the molar mass which is near 116. For that reason we decided there must be another element there and the most obvious was O.

Now it doesn't matter whether you agree about this, or whether (as I am beginning to think) the guys who set the problem made a mistake or you miscopied it, if from the data you can't reason something out about what the formula of a substance containing C, H, and O must be using the given information, then you do have a problem with elementary chemistry that you need to address. So I propose we continue the reasoning to see the answer we can get.

I mentioned the need to use all information. It is a help that there is so little. But anyway you know that to get a molecular formula from the empirical formula you need the molar mass, so you know what to look for.

Do you know what you need now to get a molecular formula in the C4 compound and the other possibles if the molecule, contains only C, H and O?
 
  • #68
I have not copied it wrong, I can scan the test paper to show you if you think I miscopied it. Also, I have done exactly what is said in the textbook. The textbook I used is Addison-Wesley Chemistry 11 ISBN: 0201708124 http://toronto.canadianlisted.com/b...11-ontario-edition-25-north-york_1749785.html. If you think I have a problem with elementary chemistry, why don't you tell me what you think is the answer then ? if you don't, then you're just as lost as me.
 
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  • #69
ghostanime2001 said:
let me just ask, do you already know the answer ? I have read it over 3 times and I still do not know what other information I'm missing. We won't get into the matter of oxygen in the compound, as you've already established that. How would I know there exists another unknown element without knowing the mass of the unknown compound. I have used all the information I'm given, I don't see any other information that I have missed. Maybe it said only "carbon-hydrogen analyzer" so I assume there is carbon and hydrogen ONLY ?

We've already been through that! With only C and H you got C8H20 - this fits the molar mass but you realized it was chemically impossible. So we concluded it must be from a smaller molecule with the given C/H ratios, and have now narrowed the possibilities to three. But with the numbers of C and H atoms in those cases we don't make the molar mass which is near 116. For that reason we decided there must be another element there and the most obvious was O.

Now it doesn't matter whether you agree about this, or whether (as I am beginning to think) the guys who set the problem made a mistake or you miscopied it, if from the data you can't reason something out about what the formula of a substance containing C, H, and O must be using the given information, then you do have a problem with elementary chemistry that you need to address. So I propose we continue the reasoning to see the answer we can get.

I mentioned the need to use all information. It is a help that there is so little. But anyway you know that to get a molecular formula from the empirical formula you need the molar mass, so you know what to look for.

Do you know what you need now to get a molecular formula in the C4 compound and the other possibles if the molecule, contains only C, H and O, without having measured the O content?

OK as this is to slow and I will have to continue tomorrow, I hope you realize you need the approximate atomic mass of O , which probably you remember is 16. So what conclusions can you make using that?
 
  • #70
add atomic mass of oxygen to empirical formula mass ?
 
  • #71
Yanik, now I understand what you mean lol...

C2H5 is possible if combined with another element. Some hydrocarbons include halogens. But, which halogen or non-halogen element is present in the unknown compound ? How can we find out the atomic number of the unknown element ? Now the question becomes finding out the number of atoms of an unknown element before solving to get the molecular formula (C2H5Ax)
 
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  • #72
Don't add halogens, please. Add oxygen and, if you are sure you did that right, add oxygen and nitrogen.
 
  • #73
mfb said:
Don't add halogens, please. Add oxygen and, if you are sure you did that right, add oxygen and nitrogen.

I agree. If there had been anything else the questioners would have told you, and there are too many possibilities to go through. And there are regular chemical analysis methods for most of them. But they might not have told you about oxygen or even nitrogen whose analyses happen to be more difficult.

It doesn't really matter what this damned substance is (I am now convinced that the question contains a mistake). It does matter that the OP who appears to be revising chemistry, can do elementary reasoning and calculations about molecules. If he looks back he will see there was nothing difficult about the reasoning that got us from the data to the conclusion that the molecule must contain one of C2H5, C4H10 or C6H15. If you additionally assume the only other element is O it should equally be a matter of a minute to see what possible molecular formula, if any, is possible. Another kick yourself afterwards question.

If necessary, about combustion analysis I found this http://www.chem.ucalgary.ca/courses/351/Carey5th/useful/cdea.html Though personally I'd find it easier to do the calculation requested off my head than wade through it.
 
  • #74
The empirical formula with oxygen is C4H10O13. I don't know how I would add nitrogen since, I don't have the mass of the unknown compound so subtraction from 100% would not work.
 
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  • #75
ghostanime2001 said:
The empirical formula with oxygen is C4H10O13. I don't know how I would add nitrogen since, I don't have the mass of the unknown compound so subtraction would not work and there are no compounds containing oxygen.

You don't give any reasoning how you get that formula so hard to help. However with 13 O atoms that empirical formula is also a minimum molecular formula, and it should hit you in the eye that that gives you way more than the molecular weight of 116. But more serious I can't see any way you could possibly get that 13, there must be some mistake. Are you using the molar mass?
 
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  • #76
You could try it yourself. I have attached my paper showing my method. I can send you the file, if it's hard to read on here. If I assume 100 g of the compound, then I can use subtraction to find the mass of oxygen and it turns out to be around 40-41 g
 

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  • #77
ghostanime2001 said:
You could try it yourself. I have attached my paper showing my method. I can send you the file, if it's hard to read on here. If I assume 100 g of the compound, then I can use subtraction to find the mass of oxygen and it turns out to be around 40-41 g

I can read it and I am sorry but you are repeating an error that was pointed out in #20, 27, 30 and elsewhere - you cannot find the original amount of oxygen in the compound from the amount in the combustion products. Some of it may have come from the compound and some or all of it from the air, we don't know how much of each.

Then you know how many moles of C and H there are in a mole of the compound - at least we have 3 different possibilities. So if all the rest in a mole of compoiund is O, as we are assuming, can't you work out how many moles that must be? 100g has nothing to do with anything.
 
  • #78
I don't know what 3 possibilities you are referring to. We can't be sure we have a mole of the compound, we not given any information concerning it's mass. If you are talking about something else concerning oxygen then please be more specific.
 
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  • #79
ghostanime2001 said:
I don't know what 3 possibilities you are referring to. We can't be sure we have a mole of the compound, we not given any information concerning it's mass. If you are talking about something else concerning oxygen then please be more specific.

Oh dear, the three possibilities it took a lot to lead you to and have been said in #63, 73. The molar mass of the compound has been stated repeatedly starting by you in#1!
 
  • #80
if you mean that adding oxygen atoms to C2H5, C4H10 and C6H15 until the correct molar mass is obtained then it either the molar mass is below the required molar mass or too high.
 
  • #81
ghostanime2001 said:
if you mean that adding oxygen atoms to C2H5, C4H10 and C6H15 until the correct molar mass is obtained then it either the molar mass is below the required molar mass or too high.

I think that's it. Could you be more specirfic, e.g. with numbers?
 
  • #82
finding x until C2H5Ox = 116.28 g/mol, C4H10Ox = 116.28 g/mol, C6H15Ox = 116.28 g/mol
 
  • #83
ghostanime2001 said:
finding x until C2H5Ox = 116.28 g/mol, C4H10Ox = 116.28 g/mol, C6H15Ox = 116.28 g/mol

So find the x.
 
  • #84
x=5.455 for C2H5Ox, x=3.6425 for C4H10Ox, x=1.83 for C6H15Ox
 
  • #85
ghostanime2001 said:
x=5.455 for C2H5Ox, x=3.6425 for C4H10Ox, x=1.83 for C6H15Ox

And can the numer of O atoms in the molecule be fractions like those?
 
  • #86
x=5.455=1091/200, x=3.6425=1457/400, x=1.83=183/100
 
  • #87
ghostanime2001 said:
x=5.455=1091/200, x=3.6425=1457/400, x=1.83=183/100

I don't know what that's about. The question was, can you have fractions of an atom?
 
  • #88
no fractions, they can only be whole numbers
 
  • #89
ghostanime2001 said:
no fractions, they can only be whole numbers

OK, so this was why some of us concluded time ago that the coompoud could not be made of C, H and O alone and there must be something else and we looked at N.

Now to make sure you understand how to do this, suppose we make the hypothesis that there is H, C and N alone, no O. Can you show us the calculation with this to find what possibilities there are for the molecule with C, H and N?
 
  • #90
x=6.234 for C2H5Nx, x=4.163 for C4H10Nx, x=2.091 for C6H15Nx
 
  • #91
ghostanime2001 said:
x=6.234 for C2H5Nx, x=4.163 for C4H10Nx, x=2.091 for C6H15Nx

OK, so what conclusion do you draw from that?
 
  • #92
there is nitrogen in the compound C6H15N2 ?
 
  • #93
ghostanime2001 said:
there is nitrogen in the compound C6H15N2 ?

Yes you could suspect that.

It is a slightly difficult one. The question is whether that 0.09 (I haven't checked) excess is significant.

As a source I believe I gave earlier http://www.chm.davidson.edu/vce/stoichiometry/ch.html says "Be aware that the elemental analysis is not perfectly accurate. The experimental error will generally produces atom ratios that are not perfect integers but are close to integers." But it doesn't give any details of accuracy to be expected from the combustion method. I'm think it is pretty accurate, and am fairly sure that nearly 5% deviation is enough to say that that is not a whole number. Yes it is surely more accurate than that and any problems would have to do with the sample. Comments by others invited.

So let us consider the remaining possibility that we have C, H, O and N and see if we get anything more convincing. Can you work out some possibilities?

Hint: actually I think you will find it easier to see where you are going if you use just the whole-number approximations to atomic masses for now.
 
  • #94
so you mean like varying the number of N and O atoms until I get something close to 116.28 g/mol ?
 
  • #95
ghostanime2001 said:
so you mean like varying the number of N and O atoms until I get something close to 116.28 g/mol ?

Yes. As I said, 116 would do and would be faster. There are not very many possibilities.
 
  • #96
C2H5O2N4 = 117 g/mol
C4H10ON3 = 116.17 g/mol
C6H15ON = 117 g/mol
 
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  • #97
:approve: One of those is more convincing and is very close to the molar mass given in the problem, though not quite exact.
I can't be here continually so more comment later.
 
  • #98
Let me draw threads together and point out some issues.

First treating this as slightly more-than-average hard exercise routinely posed to students. What I do is I believe what I'm told, suppose accuracy of measurements good. Atomic masses are near whole numbers and it is faster, you will see, if I work with those at first. The analysis gives me a C/H ratio close to 2/5 - an empirical formula you could say C2H5. Then C8H20 fits the actual molar mass of the compound. But chemically no such compound is possible. We then looked for a smaller molecule with the same C/H ratio, but with O and/or N to make up the molar mass to 116. Initial candidates must be based on C2H5, C4H10 and C6H15. Using the whole-number atomic mass approximation I rapidly eliminate the first and third of these. These part-molecules having an odd number molar mass, combined with any number of O or N which have even number mass (16 and 14) cannot make the molar mass of 116 which is even. That narrows it down to C4H10 with approximate mass 58. From 116 we need to make up 116 - 58 = 58 with O and N. 58 is not a multiple of either 16 or 14, so only with both could we find an answer. From 58 subtract 16 once, twice, three times and see if any result is a multiple of 14. Turns out the only one corresponds to N3O. So we would conclude the molecule is C4H10N3O. When I calculate the exact molar mass of that I get 116.14. That would normally be considered excellent and conclusive agreement with the #1 question figure of 116.28 but more anon.

The didactic point is that this is just an example calculation of the kind students are required to perform, usual principles, though slightly more complex than average. I cannot see anything not straightforward and even obvious about it (at most you might miss some shortcut) and do not understand why it took so long. Maybe the student now realizes what point he was missing and needs to do some more exercises to make sure he is at ease with them.

There are however some dubious points. My calculated molar mass of 116.14 is extremely close to 116.28 but we are not really comparing theory with experiment which is approximate - we are comparing theory with theory. You would only work out a figure like that from a composition and the precisely known atomic masses, so I don't know what explains the discrepancy. It is possible that this was an invented school exercise, and the authors thought of C8H20 not noticing it was impossible. For that I calculate a MM of 116.24 which is nearer though still not quite the one of the problem. At this point I should say the atomic masses that are used in such calculations are updated from time to time. I am using
H 1.00794, C 12.010107, N 14.00674, O 15.9994 Perhaps someone will check, if there are other figures around.

Molecular masses as far as I know are these days mostly determined by mass spectroscopy. But then from the fragments you can determine the composition too, and for that matter the molecular structure from mass spectroscopy. But maybe one machine cannot do everything and I am not very familiar with the state of the art.

I said ‘believe the data’. My faith wavered a bit when the OP pointed out four formulae which were within about 1% of right. In fact my shortcut rather depends on these being ruled out beforehand. But actually you can weigh within 0.1% easily so I guess this is right (though accuracy downstream does nothing if there is a problem with the sample). But you see how critical the accuracy question is to the scope of the method. The didactic exercises like http://www.chm.davidson.edu/vce/stoichiometry/ch.html just give nice numbers and pass over this. The Addison-Wesley book cited surely devotes consideration to this question and maybe the student could re-read that bit with new appreciation. Accuracy, how to check this and what you think the experiment is telling you, problems encountered, precautions etc., essentially scientific and methodological questions enriching the bare academic exercise.

Finally I found it quite difficult to find a structure that corresponds to the formula C4H10N3O. But if we can find only one we can certainly find a number of others. Is there anything wrong with
NH2NHCCHOHCH2CH2NH OR NH2NHCCH2OCH2CH2NH?

The question looks like a mistake but it has given us some useful issues to examine.
 
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  • #99
epenguin said:
Is there anything wrong with
NH2NHCCHOHCH2CH2NH OR NH2NHCCH2OCH2CH2NH?
The last N in both molecules has just 2 bonds.
 
  • #100
I think you can tell by the nitrogen rule that an odd number of nitrogens leads to an odd number of hydrogens (or equivalents, like halogens), so I'm not convinced by this at all. Unless we have ions / radicals, which I think we discounted earlier?
 

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