So I know that aspirin is soluble in ethyl acetate when it is heated over a steam bath, but is It soluble when at room temperature?
Like dissolves like is the basic principal that governs the solubility of given substance in the gien solvent.
Aspirin is phenolic ester and also containing a carboxylic functional group (Structure shown here).
At higher temperature (steam bath temperature) aspirin molecule will be much polar due to ionization of -COOH group into -COO- and hence aspirin willbe soluble in ethyl acetate.
At room temperature though ionization of -COOH group in aaspirin is not significant still it will be partially soluble in ethyl actate through ease of H-bonding.
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