Why Are Ether and Chloroform Not Suitable Solvents for ASA?

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SUMMARY

Ether and chloroform are unsuitable solvents for dissolving acetylsalicylic acid (ASA) due to their high volatility and aprotic nature, which limits their ability to effectively solvate the compound. In contrast, isopropyl alcohol, a protic solvent, provides better solubility and stability for ASA during titration with sodium hydroxide (NaOH). The discussion emphasizes the importance of solvent choice in chemical experiments, particularly regarding solubility and reaction conditions.

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  • Understanding of solubility principles in organic chemistry
  • Knowledge of protic and aprotic solvents
  • Familiarity with titration techniques
  • Basic concepts of chemical volatility
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Chemistry students, educators, and laboratory technicians involved in organic chemistry experiments, particularly those focusing on solvent selection and titration methods.

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Homework Statement


I am trying to help my son with his experiment with asa(aspirin). He titrated asa powder that was dissolved in isopropyl alcohol with NaOH. One of the questions in the inquiry was why were ether or chloroform not used to dissolve the asa? I am not certain that the answer is related to the volatility of both ether and choloroform, relative to isopropyl alcohol, or due to the fact that the alcohol is a protic solvent rather than an aprotic solvent. Any suggestions??


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The Attempt at a Solution

 
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What is the scope of the experiment? Otherwise I am soley able to claim that it's solubility that is being referred to here. An aqueous solution of NaOH is not going to dissolve in either of those other solvents from what I know.
 

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