CHM457 FUNDAMENTAL ORGANIC CHEMISTRY

EXPERIMENT 4: Preparation of Acetylsalicylic Acid (Aspirin)

Name: Intan Nur Aida Syasya bt Johari (2022864668)

NAME OF LECTURER: Dr. NAJMAH HASSAN

DATE OF EXPERIMENT:16th NOVEMBER 2022

DATE OF SUBMISSION: 30th NOVEMBER 2022

Read and understand the procedure in the lab manual and watch the given video by following
the link below:
https://www.youtube.com/watch?v=6lFQaxiRAmI&t=10s
Objective
1. To prepare acetylsalicylic acid (aspirin)
2. To synthesize acetylsalicylic acid from salicylic acid.

Chemicals and Apparatus

i. Explain briefly how to
conduct proper
recrystallization process.
1. Add the crude product into a
25 mL Erlenmeyer flask.
2. Add a minimum amount of
hot acetyl acetate into the flask
and gently heat the
mixture on a steam bath.
3. Let it cool to room
temperature. Place the flask in
an ice bath and stir the
mixture. Scratch the bottom of
the beaker with a stirring rod.
4. Pour the mixture into a
vacuum filtration and rinse the
flask with water.
5. Set the product to dry.
Chemicals and Apparatus
i. Explain briefly how to
conduct proper
recrystallization process.
1. Add the crude product into a
25 mL Erlenmeyer flask.
2. Add a minimum amount of
hot acetyl acetate into the flask
and gently heat the
mixture on a steam bath.
3. Let it cool to room
temperature. Place the flask in
an ice bath and stir the
mixture. Scratch the bottom of
the beaker with a stirring rod.
4. Pour the mixture into a
vacuum filtration and rinse the
flask with water.
5. Set the product to dry.
Chemicals and Apparatus
i)Explain briefly how to conduct proper recrystallization process.
1. Add the crude product into a 25 mL Erlenmeyer flask.
2. Add a minimum amount of hot acetyl acetate into the flask and gently heat the
mixture on 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 bottom of the beaker with a stirring rod.
6. Pour the mixture into a vacuum filtration and rinse the flask with water.
7. Set the product to dry.
ii) Provide an image with complete labelling for product filtration step (vacuum
filtration):
Results and Discussion

i. State the function of sulphuric acid in the experiment.

In this experiment, sulfuric acid act as a catalyst that speeds up the reaction and also act as a
dehydrating agent forcing equilibrium to the right forming greater yield of ester.

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

vi. 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. Due to presence
of phenols in salicylic acid, a dark blue or purple colour will form. While, when aspirin is
tested with ferric acid, no colour will form because it is not a phenol. Therefore, the final
product can be tested with ferric acid to detect any presence of salicylic acid in the sample.

Conclusion

In conclusion, acetylsalicylic acid was synthesized from salicylic acid and acetic anhydride.
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
be 86%. 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 forms highly coloured complex, it is a positive result.

References

1. Libretexts. (2020, July 14). Synthesis of Aspirin (Experiment).

https://chem.libretexts.org/Bookshelves/Ancillary_Materials/
Laboratory_Experiments/Wet_Lab_Experiments/Organic_Chemistry_Labs/
Experiments/1:__Synthesis_of_Aspirin_(Experiment)
2. Natural Science. (2017, December 17). Synthesis and Characterization of Aspirin.
Retrieved December 04, 2020, from
https://www.odinity.com/characterization-of-aspirin/
3. Medicinal Science. (2018, March 30). Synthesis of aspirin from salicylic acid using
acetic anhydride. Retrieved from
https://labmonk.com/synthesis-of-aspirin-from-salicylic-acid-using-acetic-anhy

Questions

Answer only question 5 from the lab manual.

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

1 grain = 64.79891 milligrams

5 grains = 5 × 64.79891 milligrams

= 323.995 milligrams