SCH4U/R Lab Activity

Properties of Carboxylic Acids name _______________________________ A carboxylic acid is identified by the presence of a carboxyl group. The physical properties and reactivity of carboxylic acids are accounted for by the combination of their polar functional group and their nonpolar hydrocarbon components. Properties of carboxylic acids will be investigated, such as melting and boiling points, solubility, acidity, and reactivity with KMnO4(aq) and NaHCO3(aq). The carboxylic acids to be used are ethanoic (acetic) acid and octadecanoic (stearic) acid. The purpose of this investigation is to test theoretical predictions of some chemical properties of carboxylic acids. predict the melting point and boiling point of the two acids relative to the corresponding parent hydrocarbon predict the solubility of the two acids in polar and nonpolar solvents predict the relative acidity of the two acids in polar and nonpolar solvents predict the reactivity of the two acids with KMnO4(aq) predict the relative reactivities of the two acids with NaHCO3(aq) Reactivity with KMnO4(aq) Reactivity with NaHCO3(aq)

Prediction Table Relative mp/bp Solubility Relative acidity

Part I The melting points and boiling points of ethanoic acid and octadecanoic acid are obtained from reference resources. Observation Table 1. Melting and boiling points Melting Boiling Carboxylic Acid point (oC) point (oC) ethanoic acid octadecanoic acid Part II The solubility of each acid in polar and nonpolar solvents is determined by mixing each acid with water and with oil. Observation Table 2. Solubility in polar and nonpolar solvents Solubility Solubility Test with pH with with oil Carboxylic Acid indicator water ethanoic acid octadecanoic acid Procedure 1. Add 5 mL of water to one test tube and 5 mL of oil to another test tube. In the fume hood, using an eye dropper, add one drop of glacial acetic (ethanoic) acid to each tube. Shake each tube very carefully to mix. Make and record observations on the miscibility of the contents of each tube. 2. Still in the fume hood, add a drop of pH indicator to each of the test tubes in step 1. Record the results. 3. Follow your teachers instructions to dispose of the contents of each test tube, and clean the test tubes. 4. Repeat steps 1, 2, and 3, using a small amount of solid octadecanoic acid (as instructed). These steps do not need to be performed in the fume hood.

Part III The reactions, if any, of each acid with NaHCO3(aq), a base, and with KMnO4(aq), an oxidizing agent, are observed and compared. Observation Table 3. Reactivity with KMnO4 and NaHCO3 Reactivity with Reactivity with Carboxylic Acid NaHCO3(aq) KMnO4(aq) ethanoic acid octadecanoic acid Procedure 1. Place about 2 mL of saturated NaHCO3(aq) solution in each of two test tubes. Add 2 mL of dilute ethanoic acid to one tube, and a small amount of solid octadecanoic acid to the other tube. Shake the tubes gently to mix and observe for formation of bubbles. Record your observations. 2. Place about 2 mL of KMnO4(aq) solution in each of two test tubes. Add 2 mL of dilute ethanoic acid to one tube, and a small amount of solid octadecanoic acid to the other tube. Shake the tubes gently to mix and observe for any change in colour. Record your observations. 3. Follow your teachers instructions to dispose of the contents of each test tube, and clean the test tubes. Analysis Explain the differences in the melting and boiling points for the acids in terms of the molecular structure and intermolecular forces of each acid.

Why do the two acids possess different solubilities in polar and nonpolar solvents? Account for this difference in terms of molecular structure and intermolecular forces.

Do acetic acid and benzoic acid appear to be organic acids in this investigation? Explain why or why not, with reference to experimental reactants and conditions.

Do ethanoic acid and octadecanoic acid undergo controlled oxidation reactions? Explain why or why not.