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    Lab Report Exp. 4 CHM457 Fund. Organic Chemistry

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    Husnul Hakim
    1. The document describes an experiment to prepare acetylsalicylic acid from salicylic acid and acetic anhydride. 2. Key results were a 177.99% yield of acetylsalicylic acid with a melting point of 140°C. 3. The purpose of concentrated sulfuric acid in the reaction is to act as a catalyst and dehydrating agent to aid the synthesis of acetylsalicylic acid from the reactants.

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    Lab Report Exp. 4 CHM457 Fund. Organic Chemistry

    Uploaded by

    Husnul Hakim
    41 views7 pages
    1. The document describes an experiment to prepare acetylsalicylic acid from salicylic acid and acetic anhydride. 2. Key results were a 177.99% yield of acetylsalicylic acid with a melting point of 140°C. 3. The purpose of concentrated sulfuric acid in the reaction is to act as a catalyst and dehydrating agent to aid the synthesis of acetylsalicylic acid from the reactants.

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    1. The document describes an experiment to prepare acetylsalicylic acid from salicylic acid and acetic anhydride. 2. Key results were a 177.99% yield of acetylsalicylic acid with a melting point of 140°C. 3. The purpose of concentrated sulfuric acid in the reaction is to act as a catalyst and dehydrating agent to aid the synthesis of acetylsalicylic acid from the reactants.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    41 views7 pages

    Lab Report Exp. 4 CHM457 Fund. Organic Chemistry

    Uploaded by

    Husnul Hakim
    1. The document describes an experiment to prepare acetylsalicylic acid from salicylic acid and acetic anhydride. 2. Key results were a 177.99% yield of acetylsalicylic acid with a melting point of 140°C. 3. The purpose of concentrated sulfuric acid in the reaction is to act as a catalyst and dehydrating agent to aid the synthesis of acetylsalicylic acid from the reactants.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    of 7

    FAKULTI SAINS GUNAAN UNIVERSITI TEKNOLOGI MARA

    CAWANGAN SELANGOR KAMPUS SHAH ALAM CHM 457 – FUNDAMENTAL


    OF ORGANIC CHEMISTRY
    LABORATORY REPORT

    NAME: MOHAMAD HUSNUL HAKIM BIN MOHD HARIS FADZILAH

    MATRIC NUMBER: 2022800758

    GROUP: AS2451M3

    EXPERIMENT TITLE: EXPERIMENT 4: Preparation of Acetylsalicylic Acid

    LECTURER: PROFESOR MADYA DR MOHD TAJUDIN B.


    MOHD ALI
    EXPERIMENT 4: Preparation of Acetylsalicylic Acid

    OBJECTIVE:
    i. To prepare acetylsalicylic acid from salicylic acid and acetic anhydride.
    ii. To determine percentage yield of acetylsalicylic acid isolated.
    iii. To determine the melting point of acetylsalicylic acid.

    INTRODUCTION:
    In this reaction, the hydroxyl group on benzene ring in salicylic acid react with acetic
    anhydride to form as ester functional group. Thus, the formation of acetylsalicylic acid is
    referred to as an esterification reaction. This reaction requires the presence of an acid catalyst,
    indicated by the H+ above the equilibrium arrows.

    At the end of the reaction, determine the percentage yield and melting point of acetylsalicylic
    acid.
    DATA:

    Mass of Salicylic Acid = 2.0176 g


    Mass of Empty Weighing Boat = 2.1875 g
    Mass of Empty Weighing Boat + Acetylsalicylic Acid = 6.8688 g
    Mass of Acetylsalicylic Acid = 4.6813 g
    Melting Point of Acetylsalicylic Acid = 140 °C

    CALCULATION:
    C7H6O3 + C4H6O3 C9H8O4 + C2H4O2

    Mol (C7H6O3) = Mass


    Molar Mass

    2.0176
    = = 0.0146 mol (given)
    138.1

    Density (C4H6O3) = Mass


    Volume
    1.06 = mass
    5.0
    Mass (C4H6O3) = 5.3 g
    5.3
    Mol (C4H6O3) = = 0.0519 mol (given)
    102.1

    1 mol C4H6O3 1 mol C7H6O3


    0.0519 mol C4H6O3 0.0519 mol C7H6O3
    (needed)

    Mol C7H6O3 given (0.0145) < mol C7H6O3 needed (0.0519)


    Limiting reactant = C7H6O3 (salicylic acid)
    Mol of Acetylsalicylic Acid:

    1 mol C7H6O3 1 mol C9H8O4


    0.0146 mol C7H6O3 0.0146 mol C9H8O4

    Mass of Acetylsalicylic Acid:


    Mass C9H8O4 = 0.0146 x 180.2
    = 2.63 g

    Percentage Yield of Acetylsalicylic Acid:

    Percentage yield = Actual yield x 100


    Theoretical yield

    = 4.6813 x 100
    2.63

    = 177.99%
    DISCUSSION:
    In this experiment, we can prepare acetylsalicylic acid from salicylic acid and acetic
    anhydride with presence of an acid catalyst, indicated by the H+.
    The equation for this reaction is:

    After getting the product from above reaction, the product in test tube 1 and 2 has been test
    with ferric chloride.
    Below is the observation of product that has been test with ferric chloride:

    The percentage yield of acetylsalicylic acid has been determined in this experiment which is
    177.99%. The melting point for acetylsalicylic acid has been observed which is 140 °C. For
    the precaution step, we must handle the chemical such concentrated sulfuric acid very
    carefully because it will cause burns if it is spilled on the skin. When handling with acid, we
    must wear safety gloves to avoid the acid spilled direct on the skin. We also need to make
    sure the product was fully dried before weight it.
    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 percentage yield of
    product is 177.99% and the melting point is 140 °C.

    QUESTION:

    1. What is the purpose of the concentrated sulfuric acid used in the first step?
    - Indicator for the reaction and to activate the reaction by making anhydrous acetic acid
    more reactive.
    2. What would happen if the sulfuric acid were left out?
    - The reaction would be slower and significantly more reversible such that the yield of
    aspirin is significantly decreased.
    3. If you used 5.0 g of salicylic acid and excess acetic anhydride in the preceding synthesis
    of aspirin, what would be the theoretical yield of acetylsalicylic acid in moles, grams?

    4. What is the equation for the decomposition reaction that occur with aspirin?
    5. Most aspirin tablets contain five grains of acetylsalicylic acid. How many milligrams is
    this?
    - 325 mg
    6. A student performed the reaction in this experiment using a water bath at 90°C instead of
    50°C. The final product was tested for the presence of phenols with ferric chloride. This
    test was negative; however, the melting point of the dry product was 122-125°C. Explain
    these results as completely as possible.
    - Phenolic group is not present in it which justifies the negative result on performing
    the ferric chloride test.
    7. If the aspirin crystals were not completely dried before the melting point was determined,
    what effect would this have on the observed melting point?
    - Melting point will be lowered.

    REFERENCE:

    1. Study.com | Take Online Courses. Earn College Credit. Research Schools, Degrees &
    Careers. (n.d.).
    https://homework.study.com/explanation/a-student-performed-the-synthesis-of-aspirin-
    using-a-water-bath-at-90c-instead-of-50c-the-final-product-was-tested-for-the-presence-
    of-phenols-with-ferric-chloride-this-test-was-negative-no-color-o.html

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