Theoretical Yield Calc: Asprin (C9H8O4)

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The discussion revolves around calculating the theoretical yield of aspirin (C9H8O4) from the reaction between salicylic acid (C7H6O3) and acetic anhydride (C4H6O3). The user struggles with determining the limiting reagent due to the lack of density information for acetic anhydride, which is necessary for converting volume to mass. Suggestions include calculating the stoichiometric number of moles of acetic anhydride and estimating its density based on typical values for organic compounds. The conversation highlights the importance of knowing the density to proceed with the calculations effectively. Ultimately, the problem remains unresolved due to insufficient data provided in the homework statement.
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Homework Statement


Calculate the theoretical yield of aspirin (C9H8O4).
C7H6O3 + C4H6O3 --> C9H8O4 +C2H4O2
Mass C7H6O3 = 2g
Volume C4H6O3 = 4mL


Homework Equations





The Attempt at a Solution


I am not sure where to go with this prolem at all. I can't just assume that the density of C4H6O3 is 1g/mL because it's not water, and the problem doesn't say to assume its density to be the same as water. All I could do was find the molar mass of each substance:

C7H6O3 = 138.13g/mol
C4H6O3 = 102.1g/mol
C9H8O4 = 180.17g/mol
C2H4O2 = 60.06g/mol

I also know that I have to find the limiting reagent, to actually determine the mass of C9H8O4, but doing that requires some more information. I know that I can just Google the density of C4H603, but if its not given in the problem then its assumed that there is another way. From what I know about calcualting the limiting reagent, you need either:
(1) mass reactant / molar mass reactant --> we don't have the mass of C4H603
OR
(2) volume reactant * density reactant / molar mass reactant --> we don't have the density of C4H603 either

So with the information provided, I have no idea how to calculate the mass of C9H8O4 (aspirin)
 
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Do you have the correct answer? It's been a while since I've done this but I'm sure I can help you figure it out.
 
Wax said:
Do you have the correct answer? It's been a while since I've done this but I'm sure I can help you figure it out.

No, we aren't given the answers for these problems.
 
Is the reaction balanced?
 
Yes it is.
 
Is this due tomorrow?
 
It's due on Thursday, but there are no office hours until after the work is due, for some reason. If all else fails, I will just use the density that I found on Google for the acetic anhydride
 
kathyt.25 said:
It's due on Thursday, but there are no office hours until after the work is due, for some reason. If all else fails, I will just use the density that I found on Google for the acetic anhydride

Cool, we still got some time then. :biggrin:
 
This is general chemistry 1 right? I have a book, let me open it up.
 
  • #10
Okay nevermind. LOL It's been too long for me. :X
 
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  • #11
In general problem - as stated - can't be solved for the reasons OP pointed out in the first post. However, you know number of moles of salicylic acid. Try:

1. Calculate stoichiometric number of moles of acetic anhydride.
2. Calculate mass of stoichiometric anhdyride.
3. Assuming 4 mL of anhdyride mass is that you calculated iin point 3 - what would be the density of the pure anhydride?
4. Have you ever seen an organic compound with that density? Does it look realistic?
5. If not - what will be the reasonable mass of the 4 mL? Higher than stoichiometric? Lower than stoichiometric?
6. So, what is in excess?

Could be that's off and that's not what you are expected to do, but for me that gives clear answer to the problem.

Anhydride density is very close to 1 g/mL.
 
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