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LABORATORY REPORT

FOR

FUNDAMENTAL ORGANIC CHEMISTRY CHM457

Experiment 4

‘THE PREPARATION OF ACETYLSALICYLIC ACID

(ASPIRIN)’

Details of the student:

Name: NURUL SYAMIMI BINTI ZAINAL
Matrix no: 2020809982
Lecturer’s name: MADAM FAZNI SUZILA BINTI ABDUL GHANI
Submission date: 26/11/2020

Evaluation criteria:
Total marks: 20
Marks given:
Report ------/15
Skill -----/ 5

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Experiment 4: Preparation of Acetylsalicylic Acid (Aspirin)

Objectives

i. To prepare the acetylsalicylic acid (aspirin) from salicylic acid and acetic anhydride.

ii. To identify the reaction mechanism involve on the formation of acetyl salicylic acid
upon reacting salicylic acid with acetic anhydride in acidic condition.

Chemicals

• 2.0 g of salicylic acid

• 5.0 ml of acetic anhydride
• 5 drops of concentrated sulfuric acid
• 1 drop of 1 % ferric chloride solution
• 2-3 ml of hot ethyl acetate

Apparatus

• Erlenmeyer flask
• Butchner funnel
• Butchner flask
• Test tube
• Glass rod
• Watch glass

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i. Explain briefly how to conduct proper recrystallization process

ii. Provide an image with complete labelling for product filtration step
(vacumn filtration):

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Results and Discussion

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

Sulfuric acid is added in this experiment is to act as catalyst that speeds up the
reaction and also act as dehydrating agent that forcing equilibrium to the right
forming greater yield of ester.

ii. Show the step-by-step of reactions mechanism on the formation of acetyl salicylic
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 mol= 2.0 g
Volume of acetic anhydride used = 10 ml
Isolated product yield = 86%

To find the limiting reactant,

Mass of acetic anhydride = volume × density

= 5 ml × 1.087 g/ml = 5.435 g

Mol of acetic anhydride = mass / molecular weight

= 5.435 g / 102.1 g/mol = 0.0532 mol

Mol of salicylic acid = mass / molecular weight

= 2.0 g / 138.1 g/mol = 0.0145 mol

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Therefore, salicylic acid is the limiting reactant while acetic anhydride is in excess.
1 mol of salicylic acid is equal to 1 mol of acetylsalicylic acid.
Thus, only 0.0145 mol of acetylsalicylic acid (aspirin) is produce from this experiment.

Theoretical yield of acetyl salicylic acid = molecular weight × no of mol

= 180.2 g/mol × 0.0145 mol
= 2.6129 g

𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
Percentage yield of acetyl salicylic acid = × 100
𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑

𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
86 % = × 100
2.6129

Actual yield of acetyl salicylic acid isolated = 2.6129 × (86/100)

= 2.247 g

iii. Confirmation of the product (aspirin) as compared to starting material of

salicylic acid can also be tasted using Ferric chloride. Explain this statement.

Ferric chloride (FeCl3) is used to test the purity of the collected acetyl salicylic
acid. Generally, salicylic acid contains a phenol group while acetyl salicylic
acid does not. Then if Ferric chloride is added to the aspirin, if there is purple
colour observed then that’s mean there is still some salicylic acid present and
this indicate the product is impure.

Conclusion

In conclusion, 2.247 g acetyl salicylic acid (aspirin) is produced from the reaction of
salicylic acid and acetic anhydride. From the experiment, the reaction mechanism
involved under the acid condition is observed which sulfuric acid is used as catalyst.
The percentage yield obtained is 86% which is suitable for quantitative analysis.

References

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

ii. https://pages.mtu.edu/~kmsmith/SYP/Student/Tuesday/Aspirin.pdf

iii. https://laney.edu/cheli-fossum/wp-content/uploads/sites/210/2012/01/8-Synthesis-
of-Aspirin.pdf

Question

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

If 1 grain = 0.0648 g = (0.0648 × 1000) = 64.8 mg

Then, 5 grains of acetylsalicylic acid = 5 × 64.8 = 324 milligrams,mg

CHM457_OCTOBER 2020_ODL LAB ASSESSMENT