Investigation of Benzoic Acid

From the creative mind of Mr. Sogo                                                         

                                                                      

Procedure:

1.  Place approximately 0.3 grams solid benzoic acid (structure shown above) in a 10-cm test tube.  Add a single drop of phenolphthalein solution to the test tube.

2.  Fill the test tube about half-full of distilled water and agitate to try to dissolve the solid.  When you are confident that agitation will serve no further purpose, stop agitating.  Use a piece of pH paper and forceps to test the pH of your benzoic acid “solution”. 

3.  Set up a bunsen burner, and with goggles firmly in place, heat your test tube to a gentle boil.  Start by heating at the middle of the test tube at the water level and work your way down to the bottom of the test tube.  Continue heating until you have a nice, clear solution.  Be very careful here--it is quite easy to have the test tube boil over in a sudden rush--try to avoid this by heating gently, but also keep yourself in a position where you won't be burned if it does boil over.

4.  Once you have the clear, hot solution, carefully test its pH.  Then allow the tube to cool without disruption for 5 to 10 minutes in a test tube rack.  Periodically look for evidence of crystallization. While you wait, ponder question #1 on the back of this page.

5.  When you are confident that the crystallization is complete (and the temperature has returned to near room temp), obtain a single pellet of solid NaOH.  Add this pellet to the tube and see what the NaOH does to your benzoic acid crystals.  Allow the NaOH to act "on its own" for a couple minutes.  While you wait, discuss questions #2 & #3 on the back of the page.

6.  Agitate the tube to mix everything together. Then consult with your instructor to see whether you may proceed.

7.  Your task is now to return your material to the nice, crystalline state that you had in the beginning of step 5.  You may have access to anything in the chem stockroom.  Discuss your chosen method with your group to make sure everyone is in agreement before actually carrying out the experiment.  Make sure that you get crystals in the end, not some cheap imitation.

 

Write-up instructions:  On a separate sheet(s) of paper thoroughly answer the questions.  Give thoughtful explanations when requested.  Your explanations should include chemical equations and/or molecular pictures. 
Questions to be pondered as you do the experiments and answered for the write-up: (Use this page for your notes, not the final copy.)

1.  Your pH test results should show that the solution becomes more acidic (lower pH number) when heated.  This lower pH value means there are more free H+ ions in the solution.

a)  Which H in the benzoic acid molecule is able to “come off” as an H+ ion?  Explain briefly.

b)  Why would there be more free H+ ions when the temperature is raised?  Try to bring your explanation down to the molecular level.

c)  Is there any reason why having more free H+ ions would result in the benzoic acid molecules becoming dissolved?  Hint:  in order to be a solid, the benzoic acid molecules have to snuggle up close to neighboring benzoic acid molecules. Think about what the leftover molecule looks like after the H+ breaks free and decide whether two of them would be “friendly neighbors”. 

 

2.  Draw pictures for what you think happens when sodium hydroxide meets the benzoic acid molecules, and give a hypothesis for how this relates to the benzoic acid molecules dissolving. Hint:  the sodium ion is purely a spectator in this reaction!  You can leave it out of the picture.

 

3.  Where does the pink color come from, and why does it appear in the particular location it does?

 

4.  Can the pink color co-exist with crystals (or flakes) of solid benzoic acid?  Explain.