Question

CH3CH2CH=CHCH2CH3 + KMnO4 -----------> 2 CH3CH2COOH + MnO2 The product of this reaction is a carbooxylic...

CH3CH2CH=CHCH2CH3 + KMnO4 -----------> 2 CH3CH2COOH + MnO2

The product of this reaction is a carbooxylic acid. What reaction can be done to make this product more soluable in water?

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Answer #1

The product of this reaction is propanoic acid. This compound is miscible with water, but its solubility properties can be modified according to the chemical environment of the system.

We know that carboxylic acids lose a proton in solutions where the pH value is greater than the pKa value. When a carboxylic acid, lose a proton, it will generat two charged species. In this case, for propanoic acid at pH values greater than 4.88:

The shown equilibrium tends to the right, and those species are soluble in water.

Finally, to make this product more soluble in water we must add a weak base to deprotonate the carboxylic acid

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