Benzene, C6H6, is a hydrocarbon found in crude oil, and a major component of gasoline. It's used to make synthetic fibers, detergents and even drugs. You can derive benzoic acid, chemical structure C6H5COOH, from benzene by uniting of the water insoluble benzene molecule with a carboxylic acid group, (-COOH). This produces a water-soluble, pleasant-smelling white powder that is used for flavorings and perfume. The formation of benzoic acid has to do with “ionizability.” Water can attach to benzoic acid by hydrogen bonding. Beyond that, water molecules can stabilize the formation of the “benozate” ion.
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Benzoic acid has low solubility in room-temperature water because the bulk of the molecule is non-polar. At higher temperatures, solubility increases.
Primary Reason for Low Solubility
The primary reason benzoic acid dissolves only slightly in cold water is that, even though the carboxylic acid group is polar, the bulk of the benzoic acid molecule is non-polar (water is polar). It is only the carboxylic group that is polar. In addition, there are no internal stabilizing structures that favor carboxylate, -COO(-), over carboxylic acid, -COOH.
When not in the presence of water, two molecules of benzoic acid may form what is called a dimer. In this instance, one molecule hydrogen-bonds to the second molecule.
In the presence of water, though short of ionization, water can hydrogen bond to benzoic acid. Thus:
C6H5COOH + H2O → C6H5COO--H--OH2.
Such a hydrogen-bonded species may go to the point of ionization.
Beyond hydrogen bond formation, full ionization can take place if there is some causative agent to force this. Bases can force ionization, but to a limited degree water produces ionization, according to the following reaction equation:
C6H5COOH + H2O → C6H5COO(-) + H3O(+)
Ionization guarantees water-solubility, since water is a polar solvent.
Heat Increases Solubility
Adding heat greatly increases solubility because some of the increased energy sufficiently lengthens the hydrogen-bonds, so that ionization occurs. Ions are by definition polar, so the general truism, like dissolves like, indicates the ions will then dissolve in water.
In addition to temperature changes, there are other ways to increase or decrease the water-solubility of benzoic acid. The addition of a strong acid decreases the ionization through the “common ion” effect. Increasing the pH increases ionization of the benzoic acid, perhaps leading to reaction.
Benzoic Acid and Other Solvents
Although its solubility in water is low, benzoic acid is soluble in other solvents. Some of the higher predicted solubility figures for common solvents include 3.85M for hexane and 9.74M for ethyl acetate.
About the Author
Vincent Summers received his Bachelor of Science degree in chemistry from Drexel University in 1973. He furthered his education through the University of Virginia's Citizen Scholar Program program, taking many courses in organic and quantum chemistry. He has written technical articles since 2010.