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CHM457 - Exp 4

This laboratory report details the synthesis of aspirin from salicylic acid and acetic anhydride with sulfuric acid as a catalyst. The student obtained an 86% yield of aspirin after purification. Ferric chloride testing confirmed the absence of phenols in aspirin indicating successful synthesis.

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1K views

CHM457 - Exp 4

This laboratory report details the synthesis of aspirin from salicylic acid and acetic anhydride with sulfuric acid as a catalyst. The student obtained an 86% yield of aspirin after purification. Ferric chloride testing confirmed the absence of phenols in aspirin indicating successful synthesis.

Uploaded by

2023406014
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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LABORATORY REPORT

FOR

FUNDAMENTAL ORGANIC CHEMISTRY CHM457

Experiment 4

This evaluation is carried out in compliance with the assessment requirements for
the subject of Fundamental Organic Chemistry CHM457 on semester of October
2020. This assessment is different from the previous semesters due to the pandemic
situation of Covid-19.

Details of the student:

Name: NURUL HIBRIYAH BINTI MUHAMMAD HILMI

Matrix no: 2023406014

Lecturer’s name: DR. MOHD TAJUDIN BIN MOHD ALI

Submission date: 19/04/2024

Evaluation criteria:

Total marks: 20

Marks given:

Report ------/15

Skill -----/ 5
Experiment 4: Preparation of Acetylsalicylic Acid (Aspirin)

Objectives

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


ii. To calculate the actual yield of acetylsalicylic acid isolated.

Chemicals and Apparatus

i. Explain briefly how to conduct a proper recrystallization process.

Initially, we mix salicylic acid (solid) from the Buchner funnel to a clean 250 mL beaker with
hot acetic anhydride (liquid) in the presence of a catalytic amount of sulfuric acid. Next, heat up
the mixture for 10 minutes at 90°C before letting the reaction mixture cool down to room
temperature. Then, we add water to induce crystallization and filter the resulting crystals to
obtain purified aspirin. If oil forms instead of solid crystals, heat the beaker in a hot water bath
until the oil disappears. If crystals do not form, you can scratch the bottom of the beaker to
encourage crystallization.

ii. Provide an image with complete labeling for product filtration step (vacuum filtration):
Results and Discussion

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

Sulfuric acid serves as a catalyst by accelerating the reaction between salicylic acid and acetic
anhydride and facilitates the formation of the ester bond, converting salicylic acid into aspirin.

ii. Show the step-by-step reaction 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%

Assume the density of acetic anhydride is 1.08 g/mL:


Mass of acetic anhydride = 10 ml × 1.08 g/mL = 10.8 g
The balanced chemical equation for the reaction:
Salicylic acid + Acetic anhydride → Sulfuric acid + Aspirin + Acetic acid
C₇H₆O₃ + (CH₃CO)₂O → H₂SO₄ + C₉H₈O₄ + CH₃COOH
𝑀𝑎𝑠𝑠 𝑜𝑓 𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑 2𝑔
Moles of salicylic acid = 𝑀𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑
= 138.12 𝑔/𝑚𝑜𝑙 = 0.0145 mol
𝑀𝑎𝑠𝑠 𝑜𝑓 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒 10.8 𝑔
Moles of acetic anhydride = 𝑀𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒 = 102.09 𝑔/𝑚𝑜𝑙 = 0.1058 mol

Limiting reactant : C₇H₆O₃, Theoretical moles of aspirin = moles of limiting reactant

Mass of aspirin (theoretical) = Moles of aspirin (theoretical) × Molar mass of aspirin


= 0.0145 mol × 180.158 g/mol
= 2.6123 g

Actual yield = Isolated product yield × Mass of aspirin (theoretical)


86
= 100
× 2.6134 g
= 2.248 g

Actual yield of acetyl salicylic acid isolated = 2.248 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.

The Ferric chloride test is a common way to detect phenols in a sample by observing a color
change when the phenol reacts with the FeCl₃. Phenols have a hydroxyl group directly attached
to a benzene ring, like in salicylic acid. Aspirin does not have -OH group, so it will not produce
a color change when tested with Ferric chloride. This test is used to confirm the presence or
absence of phenols in a sample.

Conclusion

In summary, acetylsalicylic acid was produced by combining salicylic acid and acetic anhydride
with the help of sulphuric acid as a catalyst and dehydrating agent. The experimental mass of the
product was 2.6123 g, slightly higher than the actual mass of 2.248 g, resulting in a 86% yield.
The final product was tested with ferric acid to check for the presence of salicylic acid, with a
color change indicating a positive result.
References

1. Libretexts. (n.d). 2.3: Synthesis and Recrystallization of Aspirin. Chemistry LibreTexts.


Retrieved April 13, 2024, from
https://chem.libretexts.org/Courses/Westfield_State_University/General_Chemistry_
Lab_Westfield_State/02%3A_General_Chemistry_2_(Chem0111)/2.03%3A_Synthes
is_and_Recrystallization_of_Aspirin

2. Chemistry 104: Synthesis of Aspirin. Retrieved April 13, 2024, from


http://www.chem.latech.edu/~deddy/chem104/104Aspirin.htm

3. Labmonk. (March 4, 2024). Synthesis of Aspirin from Salicylic Acid using Acetic Anhydride.
Retrieved April 13, 2024, from
https://labmonk.com/synthesis-of-aspirin-from-salicylic-acid-using-acetic-anhydride

Questions

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

1 grain : 64.8 mg
5 grain : X mg
X = 323.99 mg

So, 5 grains of acetylsalicylic acid is approximately 324 milligrams.

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