EXPERIMENT 11: SYNTHESIS OF BENZOIC ACID

IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR

CHEM 1110 (SECTION 07)

SUBMITTED TO:

DR. ALEKSANDR PIKELNY

CALIFORNIA STATE UNIVERSITY, LOS ANGELES

SCHOOL OF CHEMISTRY AND BIOCHEMISTRY

SUBMITTED BY:

LINDA KURODA

SEPTEMBER 04, 2017

FALL 2017
I. Purpose:

The purpose of this experiment is to create an organic synthesis and oxidize benzoic acid.

Then the benzoic acid will be recrystallized and evaluated of acidity with pH titration.

II. Principles:

Benzaldehyde can be oxidized when exposed to a basic solution. Aldehyde group with

the –CHO group is oxidized. In this experiment potassium permanganate will be used to oxidize

benzaldehyde. Neutral uncharged benzoic acid is formed when acid is added to the benzoate

solution. Benzoic acid is soluble at room temperature water and hydrochloric acid will cause it to

precipitate when combined. Recrystallization occurs when the solution is cooled and benzoic

acid separates from the water and particles are left behind.

III. Procedures:

1. Weigh out 5 g of sodium hydroxide into a 250ml Erlenmeyer flask with 100ml of

water and stir until dissolved.

2. Weigh 7g of potassium permanganate on a watch glass and with a spatula divide into

four equal portions.

3. Add one portion of potassium permaganate to the solution in the flask and swirl until

dissolved

4. Measure 5mL benzaldehyde into your 10ml graduated cylinder and weigh the cylinder

and benzaldehyde and record this weight to nearest 0.01g.

5. Add the benzaldehyde to the solution in the flask and re-weigh the graduate cylinder to

use this weight to calculate the amount of benzaldehyde added.

6. Stir the mixture until the solution turns into a muddy brown color.

7. Add the other portions of potassium permanganate one by one stirring each time in

between till the solution turns brown

8. Run tap water around the outside of the flask to cool the solution

9. Convert the soluble KMnO4 to insoluble MnO2 by adding 7ml of ethanol

10. Stir the mixture for 5minutes then filter to remove the MnO2

11. Set up the suction filtration apparatus shown in your lab manual and put a filter paper

into the Buchner funnel.

12. Wet the filter paper evenly and turn on the vacuum and pour the mixture into the

funnel.

13. with 5ml of distilled water rinse out any MnO2 that might be left.

14. With the clear solution left over transfer it to a 250ml beaker

15. Bring this solution under the hood and add hydrochloric acid to the solution to

precipitate it.

16. Keep adding HCl until the solution is acidic by testing it with pH strips

17. Add an additional HCl and cool the mixture and a 20ml of distilled water in an ice

bath

18. Set up the suction filtration apparatus again and pour the cooled mixture in the funnel.
 19. Rinse the remaining white powder with the ice cold 20ml of water

20. Collect the white powder left over and put it into a clean 250ml beaker and add 100ml

of water

21. Take this beaker and heat it over a Bunsen burner and stir until all of it has dissolved

22. Let cool then place in ice bath with an additional 20ml distilled water

23. Pour the cooled solution in the suction filtration apparatus and rinse with the ice cold

water that has been left to chill in the ice bath

24. Weigh the dry product at your next lab period and record this weight.

IV. Data

Mass sodium hydroxide 5.21g

Mass potassium 7.25g

permanganate
Mass watch glass 60.40g
Mass watch glass and 67.65g

potassium permanganate
Mass cylinder 26.45
Mass cylinder and benzoic 32.02

acid
Mass watch glass empty 53.97g
Mass watch glass and benzoic 58.44g

acid
Final mass benzoic acid 4.47g
% yield benzoic acid 89.4%
 4.47 g
( ) x100% = 89.4% percent yield
5.00 g

V. Results

Benzoic acid reacts with NaOH to form benzoate salt which is soluble in water. Benzoic

itself in water is insoluble due to hydrophobic benzene which interferes with the hydrogen bonds

which is needed for it be soluble.

In the manufacture of ammonia, nitrogen, and hydrogen gases react over an

iron/potassium oxide catalyst to give ammonia. Hydrogen is the expensive reagent as nitrogen

can be obtained from the air. If ammonia is obtained in 90% yield based on hydrogen, how many

tons of hydrogen are necessary to produce 100 Mg of ammonia?

N2 + 3H2 = 2NH3

(6 x 100 x 106 x 10) / 34 x 9 = 196.07 tons

During oxidation of permanganate color changes occur from purple to a muddy brown

color. The change in color is due to the reaction conversion of Mn-VII to Mn-IV.
VI. Conclusion

In this experiment we observed the changes of benzoic acid as it goes through various

reactions. Changes in color occurred from oxidation and conversion of Mn. Then

recrystallization of the benzoic acid by purifying it by heating, cooling, allowing to precipitate

and extract excess moisture. However there were a few limitations to this experiment such as

using different type of scales to weigh materials. The electric balance was much more accurate

and precise versus the triple beam balance was hard to keep calibrated and varied with each triple

beam balance. A reliable scale would solve this problem.

References

Goldwhite, H., & Tikkanen, W. (2001). Experiment in general chemistry (4th ed.). Boston, NY

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