Why Does NaHCO3 Help Dissolve Aspirin?

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The discussion centers on the role of sodium hydrogencarbonate (NaHCO3) in enhancing the solubility of aspirin (acetylsalicylic acid) in water. When aspirin is mixed with NaHCO3, a reaction occurs where the basic sodium bicarbonate deprotonates the acidic acetylsalicylic acid, forming a carboxylate anion that is highly soluble in water. Without the presence of NaHCO3, the acetylsalicylic acid remains uncharged and less soluble due to its non-polar characteristics. The reaction results in the formation of soluble sodium acetylsalicylate, carbon dioxide, and water, which promotes the dissolution of the aspirin tablet in aqueous solutions. This process is similar to the reaction between benzoic acid and sodium bicarbonate, demonstrating the general principle of acid-base reactions improving solubility in polar solvents.
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Hi ppl,
I was wondering could someone help me with this explanation. Why does the addition of Sodium Hydrogencarbonate help an aspirin to dissolve. In tablets of aspirin, acetylsalicylcic acid is mixed with sodium hydrogencarbonate and when the soluble aspirin tablet is dissolved in water the acetylsalicylcic acid and the sodium hydrogencarbonate react together.

Thanks a lot,
joe
 
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In aqueous solution the basic NaHCO3 can deprotonate the acidic acetylsalicylic acid. The resulting charged species (carboxylate anion) is very soluble in water.

Without the base then the acid would be protonated and therefore uncharged. The rest of the molecule is rather non-polar and thus not very soluble in polar solvents like water.
 
As Movies explained the issue well, I will only give the reaction scheme.

HSal + NaHCO_3 \longrightarrow Sal^- Na^+ + CO_2 + H_2O

Normally, H2CO3 is expected to be formed, but is very unstable to yield carbon dioxide and water for lower energy and higher unregularity (entropy) needs.
 
josephcollins said:
Hi ppl,
I was wondering could someone help me with this explanation. Why does the addition of Sodium Hydrogencarbonate help an aspirin to dissolve. In tablets of aspirin, acetylsalicylcic acid is mixed with sodium hydrogencarbonate and when the soluble aspirin tablet is dissolved in water the acetylsalicylcic acid and the sodium hydrogencarbonate react together.

Thanks a lot,
joe

It's very similar to that between benzoic acid and sodium hydrogencarbonate.

C6H5COOH + NaHCO3 -----> C6H5COONa + CO2 + H2O
NaHCO3
 
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