FACULTY OF APPLIED SCIENCES

LABORATORY REPORT
FUNDAMENTAL ORGANIC CHEMISTRY
(CHM 457)
Title of Experiment Preparation of Acetylsalicylic
Acid (Aspirin)
No. Experiment 4
Name of Student Norhidayu bt Adnan
Student ID Number 2021898286
Programme Code AS2532A
Date of Experiment is Done 28/04/2022
Date of Lab Report is Submitted 06/05/2022

Lecturer’s Name Dr Najmah bt P.S. Hassan

Title: Preparation of Acetylsalicylic Acid (Aspirin)

Objectives

i. To prepare acetylsalicylic acid from salicylic acid and acetic anhydride.

ii. To determine actual yield of acetylsalicylic acid isolated.

Chemicals and Apparatus

i. Explain briefly how to conduct proper recrystallization process.

1. Fill a 25 mL Erlenmeyer flask with the crude product.

2. Add the flask halfway with hot acetyl acetate and slowly heat the mixture over a
steam bath.
3. Let it cool to room temperature.
4. Place the flask in an ice bath and stir the mixture.
5. Scratch the beaker's bottom with the stirring rod.
6. Pour the mixture into a vacuum filtration and rinse the flask with water.
7. Allow time for the product to dry.

ii. Provide an image with complete labelling for product filtration step (vacuum
filtration):
Result and Discussion
i. State the function of sulphuric acid in the experiment.

Sulphuric acid functions as a catalyst, which increase the rate of the reaction, as well
as a dehydrating agent, shifting the equilibrium to the right.

ii. Show the step-by-step of reactions mechanism on the formation of acetylsalicylic acid
upon reacting salicylic acid with acetic anhydride in acidic condition.
iii. Calculate the actual yield of product from the given information:

Amount of salicylic acid used = 2.0 g

Volume of acetic anhydride used = 10 ml
Isolated product yield = 86%

Actual yield of acetyl salicylic acid isolated = g

1.06 𝑔 1 𝑚𝑜𝑙
𝑛𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒 = 5 𝑚𝐿 × × 102.1 𝑔
1 𝑚𝐿

= 0.0519 𝑚𝑜𝑙

1 𝑚𝑜𝑙
𝑛𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑 = 2.0 𝑔 ×
138.1 𝑔
 = 0.0148 𝑚𝑜𝑙

𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑 𝑖𝑠 𝑡ℎ𝑒 𝑙𝑖𝑚𝑖𝑡𝑖𝑛𝑔 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡

1 mol of salicylic acid produced 1 mol of acetylsalicylic acid

∴ 0.0148 𝑚𝑜𝑙 𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑 𝑝𝑟𝑜𝑑𝑢𝑐𝑒𝑑 0.0148 𝑚𝑜𝑙 𝑎𝑐𝑒𝑡𝑦𝑙𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑

180.2 𝑔
𝑒𝑥𝑝𝑒𝑟𝑖𝑚𝑒𝑛𝑡𝑎𝑙 𝑚𝑎𝑠𝑠 = 0.0148 𝑚𝑜𝑙 × 1 𝑚𝑜𝐿

= 2.667 𝑔

𝑎𝑐𝑡𝑢𝑎𝑙 𝑚𝑎𝑠𝑠
𝑖𝑠𝑜𝑙𝑎𝑡𝑒𝑑 𝑝𝑟𝑜𝑑𝑢𝑐𝑡 𝑦𝑖𝑒𝑙𝑑 = × 100
2.667 𝑔

𝑎𝑐𝑡𝑢𝑎𝑙 𝑚𝑎𝑠𝑠 = 0.86 × 2.667 𝑔

= 2.3 𝑔

iv. Confirmation of the product (aspirin) as compared to starting material of salicylic acid
can also be tested using Ferric chloride. Explain this statement.

Ferric chloride is used to determine the presence of phenols in a sample. This is because
a highly coloured complex will form when phenols react with ferric chloride. Salicylic
acid appears to take on a dark blue or purple colour due to the presence of phenols.
While, when aspirin is tested with ferric acid, no colour will form because it is not a
phenol. As a result, the final product can be tested with ferric acid to detect if any
salicylic acid is present.

Conclusion
As a conclusion, acetylsalicylic acid was synthesized from salicylic acid and acetic acid and
the sulphuric acid in this experiment was used as a catalyst and dehydrating agent to aid the
synthetization of acetylsalicylic acid. From the results obtained, the experimental mass of the
product is 2.667 g while the actual mass is 2.3 g. The isolated product yield is calculated to
be86%. The final product was tested with ferric acid to detect any presence of salicylic acid. If
there is no colour changes, it is a negative result due to absence of salicylic acid. While, if it
form highly coloured complex, it is a positive result
References
1. The chemistry of aspirin: The International Aspirin Foundation. Aspirin Foundation.
(2020, June 8). Retrieved May 14, 2022, from https://www.aspirin-
foundation.com/history/chemistry/#:~:text=The%20Chemistry%20of%20Aspirin%20
(acetylsalicylic%20acid)&text=Aspirin%20is%20prepared%20by%20chemical,
white%20crystals%20or%20crystalline%20powder.

2. Libretexts. (2020, July 14). 1: Synthesis of aspirin (experiment). Chemistry LibreTexts.

Retrieved May 14, 2022, from
https://chem.libretexts.org/Ancillary_Materials/Laboratory_Experiments/Wet_Lab_E
xperiments/Organic_Chemistry_Labs/Experiments/1%3A__Synthesis_of_Aspirin_(E
xperiment)

Question and Answer

1. Most aspirin tablets contain five grains of acetylsalicylic acid. How many miligrams
is this?

1 𝑔𝑟𝑎𝑖𝑛 = 64.799 𝑚𝑔
5 𝑔𝑟𝑎𝑖𝑛𝑠 = 5 × 64.799 𝑚𝑔
= 323.995 𝑚𝑔