Ingredient in aspirin is acetylsalicylic acid

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Discussion Overview

The discussion revolves around a homework problem involving the active ingredient in aspirin, acetylsalicylic acid, and its reaction with sodium hydroxide and hydrochloric acid. Participants explore the calculation of molar mass and the acid dissociation constant (Ka) based on provided experimental data.

Discussion Character

  • Homework-related
  • Mathematical reasoning
  • Technical explanation

Main Points Raised

  • One participant calculates the number of moles of acetylsalicylic acid and sodium hydroxide, both found to be 0.014 moles, but expresses uncertainty in proceeding further.
  • Another participant suggests that at the complete reaction point, the moles of sodium hydroxide equal the moles of acetylsalicylic acid, and encourages calculating the formula weight from the known mass and moles.
  • A participant describes the reaction between acetylsalicylic acid and hydroxide ions, stating that after the reaction, 0.015 moles of the deprotonated form remain, but questions how to proceed with the addition of hydrochloric acid.
  • One participant challenges the 0.015 moles figure and emphasizes the importance of correctly determining the number of moles to calculate the molar mass. They also note that the hydrochloric acid added has the same concentration as sodium hydroxide, with a volume that is half, and question the pH at this stage.
  • A later reply introduces skepticism about the reaction process, stating that acetylsalicylic acid does not react with sodium hydroxide as typically assumed and suggests that back titration may be a more reliable method due to hydrolysis concerns.

Areas of Agreement / Disagreement

Participants express differing views on the number of moles involved in the reactions and the appropriate method for calculating the molar mass and Ka value. There is no consensus on the correct approach or the validity of the assumptions made in the problem.

Contextual Notes

Some participants highlight potential limitations in the problem's assumptions, particularly regarding the reaction mechanism of acetylsalicylic acid with sodium hydroxide and the implications for accurate titration results.

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Homework Statement


The active ingredient in aspirin is acetylsalicylic acid. A 2.51 g sample of acetysalicylic acid required 27.36 mL of a 0.5106 M NaOH for complete reaction. Addition of 13.68 mL of 0.5106 M HCl to the flask containing the aspirin and sodium hydroxide produced a mixture with pH=3.48. Find the molar mass of acetylasalicylic acid and Ka value.


Homework Equations





The Attempt at a Solution


I'm not really sure what to do but first i found the number of moles of acetysalicylic acid and NaOH (which is OH-) which were both 0.014 moles and they both have an equivalence point of 0 since it goes to complete reaction...then i get kinda lost..i did a neutralization with C9H8O4 which is acetysalicylic acid with OH- and found the Molar mass of C9H8O4- to be 0.014/v M because we don't know the total volume...then i get lost...
 
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At the point where you have 'complete reaction' of the NaOH with ASA, the number of moles of sodium hydroxide equals the number of moles of ASA. So you know moles and the mass (2.51g). Calculate the FW from that. Volume for the base is 27.36 mL. That is the only important volume in your problem.

Remember that pH = -log[H+] and that Ka = [ASA-][H+]/[ASA]

Any help?
 


chemisttree said:
At the point where you have 'complete reaction' of the NaOH with ASA, the number of moles of sodium hydroxide equals the number of moles of ASA. So you know moles and the mass (2.51g). Calculate the FW from that. Volume for the base is 27.36 mL. That is the only important volume in your problem.

Remember that pH = -log[H+] and that Ka = [ASA-][H+]/[ASA]

Any help?
well what i did is:
C9H8O4 + OH- --> C9H8O4- +H20..from that i found that the moles is 0.015 and since they're equal, both reactants cancel and all that is left is 0.015 moles of C9H8O4- (which i then divided by 27.36 mL converted into liters).

then what? do i do a buffer with C9H8O4- or do i use the HCl onto that? Thanks.
 


I can't see 0.015 moles here.

Once you will know correct number of moles, combine it with the sample mass to calculate molar mass.

Note, that HCl added has identical concentration with NaOH, and that volume used is exactly half that of NaOH. Do you know phH of acid neutralized only in half?

Finally, when you will solve the question, you should forget it as fast as possible. ASA doesn't react with NaOH in the way whoever wrote the question imagines. It hydrolizes fast enough to make this titration difficult if not impossible. The most reliable method calls for back titration - addition of excess NaOH, hydrolyzis (they don't react 1:1 then) and titration of the excess HCl.
 

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