Question

Rank these organic compounds in terms of increasing water solubility (from least water soluble to most water soluble).

Short answer

Rank of these organic compounds areB<C<A

Step-by-step solution

Solubility of molecules in a solvent

When we talk about the solubility of molecules in a solvent, there is a simple empirical rule that can help us determine solubility in any given solvent.

The empirical rule is "like dissolves like" and it is based on the polarity of the system. That is, polar molecules dissolve in polar solvents.

Rank the compound based on solubility

Carboxylic acids are more polar than ketones, and considering that each carboxylic acid can form two hydrogen bonds with two water molecules, we can say with certainty that carboxylic acids are more soluble in water than ketones.

Next, the ketone is more polar than the alkene. A ketone with its carboxyl group can form a single hydrogen bond with a water molecule. Therefore, ketones have greater water solubility than alkenes.

Therefore, we can say that compound B is the least water soluble, and compound A is the most water soluble.

Hence, rank of compound is B<C<A