Exploring Solvents for ASA: Why Not Ether or Chloroform?

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In summary, a parent is seeking help with their son's experiment involving titration of asa powder dissolved in isopropyl alcohol with NaOH. They are unsure why ether or chloroform were not used to dissolve the asa and are wondering if it is due to the volatility of these solvents or the fact that isopropyl alcohol is a protic solvent rather than an aprotic solvent. The experiment is focused on solubility and it is noted that an aqueous solution of NaOH will not dissolve in ether or chloroform.
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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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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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There are a few reasons why ether and chloroform may not be suitable solvents for dissolving ASA. First, as you mentioned, both ether and chloroform are highly volatile solvents which can be hazardous to work with. Additionally, they are both flammable, which could pose a safety risk during the experiment.

Another factor to consider is the polarity of the solvents. ASA is a polar compound, meaning it has a positive and negative end. In order to dissolve it, a polar solvent is needed. Isopropyl alcohol is a polar solvent, while ether and chloroform are nonpolar solvents. This means they may not be able to effectively dissolve the ASA, resulting in inaccurate titration results.

Furthermore, as you mentioned, isopropyl alcohol is a protic solvent, meaning it has a hydrogen atom that can form hydrogen bonds with the ASA molecules. This allows for better solvation of the ASA and helps to stabilize it in solution. Ether and chloroform are aprotic solvents, meaning they do not have a hydrogen atom available for hydrogen bonding. This could also contribute to the difficulty in dissolving the ASA in these solvents.

In conclusion, the choice of isopropyl alcohol as a solvent for dissolving ASA is likely due to a combination of factors, including safety, polarity, and the ability to form hydrogen bonds. I hope this helps to clarify the reasons behind the choice of solvent in your son's experiment.
 

FAQ: Exploring Solvents for ASA: Why Not Ether or Chloroform?

1. What are the main properties of ether and chloroform that make them unsuitable solvents for ASA?

Ether and chloroform are both highly volatile and flammable solvents, which can pose a safety hazard in a laboratory setting. Additionally, ether has a relatively low boiling point and chloroform is known to have toxic effects on the liver and other organs.

2. Are there any other solvents that have similar properties to ether and chloroform but are safer to use?

Yes, there are several alternatives to ether and chloroform that have similar properties but are safer to use. For example, diethyl ether can be replaced with diisopropyl ether, and chloroform can be substituted with dichloromethane. Both of these solvents have higher boiling points and are less toxic.

3. Can ether or chloroform be used in small quantities as co-solvents for ASA?

While it is possible to use small quantities of ether or chloroform as co-solvents for ASA, it is generally not recommended. The potential hazards associated with these solvents outweigh any benefits they may provide in terms of solubility or reaction rate.

4. Are there any alternative solvents that have been successfully used in place of ether or chloroform for ASA reactions?

Yes, there are several alternative solvents that have been successfully used for ASA reactions. Some examples include acetone, ethyl acetate, and acetonitrile. These solvents have similar properties to ether and chloroform but are less hazardous.

5. Can the choice of solvent affect the overall yield or purity of ASA?

Yes, the choice of solvent can have a significant impact on the yield and purity of ASA. Using a solvent that is not compatible with the reaction conditions or that produces unwanted by-products can result in a lower yield and lower purity of the final product.

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