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    asipirin organic lab report

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    Elias Biramo

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    asipirin organic lab report

    Uploaded by

    Elias Biramo
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    2 views7 pages

    asipirin organic lab report

    Uploaded by

    Elias Biramo

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    © All Rights Reserved
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    TITLE:THE SYNTHESIS AND ANALYSIS OF ASPRIN

    Objective :to synthesize aspirin and determine its


    quality

    Theory :

    Acetylsalicylic acid commonly known as aspirin is the most widely used drug
    in the world today. Its analgesic, antipyretic, and anti-inflammatory properties
    make it a powerful and effective drug to relive symptoms of pain, fever, and
    inflammation. It is a synthetic organic product derived from salicylic acid with
    acetyl chloride or acetic anhydride in the presence of catalytic. Salicylic acid is
    a natural product found in the bark of the willow tree and was used by the
    ancient Greeks and Native Americans, among others, to counter fever and
    pain. However, salicylic acid is bitter and irritates the stomach. The reaction
    that is used for the synthesis is shown below.

    In this reaction, an excess of acetic anhydride (C4H6O3) is added to a


    measured mass of salicylic acid (CH6O3) in the presence of a catalyst, sulfuric
    acid (H2SO4).
    The reaction involves the conversion of a phenol to an ester. This reaction is
    reversible, which is why aspirin commonly smells of vinegar, as the ASA
    hydrolyzes in air back to SA and acetic acid. Since acetic acid is very soluble in
    water, it is easily separated from the aspirin product. The aspirin isolated in this
    step is the "crude product". A "purified product" can be obtained through
    recrystallization of the crude product in hot ethanol. In this experiment, the crude
    product will be the desired product. The percent yield of the crude product will be
    determined or this reaction. The purity of the product will also be analyzed.
    Apparatus Used

    - Beaker
    - Test tube
    - Beaker Glass rod
    - Filter paper
    - Buchner Funnel
    - Water bath

    Chemicals Used

    - Salicylic acid
    - Acetic anhydride
    - Sulphuric acid
    - Ferric chloride
    - Distilled water
    - Ethanol
    Procedure

    Part A - Aspirin Synthesis

    Preparing the starting Materials

     1g of salicylic acid was added into a clean test tube.


     Using the Micropipette or Pipette we carefully added 2.5mL of acetic
    anhydride to the test tube
     then 3 drops of concentrated sulfuric acid was added as a catalyst
     After gently swirling, and the flask was placed in hot water bath and
    flask was clamped to a ring stands and heated for 10 minutes.
     a glass rod was stirred constantly until the entire solid was completely
    dissolved.

    Cooling the Reaction Mixture

    the flask was removed from the boiling water bath and was allowed cooling
    to room temperature.
    After the flask has cooled for about 3 minutes, the mixture was poured to a
    beaker that contains 30 ml of water to facilitate the decomposition of the
    excess acetic anhydride.
    The flask was swirled to mix the contents.
     flask was placed it in an ice bath and cooled until the crystallization of the
    aspirin appears complete (approx. 20 min.).

    Isolating the Product

     Then aspirin was collected using a Buchner funnel and filter paper.
     the filter paper was seated in the filter with a small amount of water
     the flask was rinsed twice with 5 mL of ice-cold water to remove
    residual crystals.

    Drying the synthesized Aspirin

     the filter paper was removed carefully with the product and placed in a
    paper box. then was lifted to dry in the hood till next week.
    Part B: Analysis of synthesized Aspirin
    1. Solubility test

     a small amount of the dry crystals of prepared aspirin was taken on the tip of
    a spatula,
     and was putted in a small test tubes which containing 1 ml of the test
    solvent water, ethanol and 10% sodium bi carbonate solution.
     Then the same procedure was repeated using salicylic acid and commercial
    aspirin

    A Test for the phenolic hydroxyl group.

    three test tubes was labeled, a few crystals of salicylic acid was placed into
    test tube number 1, a small sample of prepared aspirin into test tube
    number 2, and a small sample of crushed commercial aspirin into number
    3.
    Then 1mL of ethanol was added to each test tube and then was swirled to
    dissolve the crystals.
    Then 1drop of 1% ferric chloride was added to each test tube.

    OBSERVATION
    When we observed that the prepared aspirin has some impurities because when
    we test the aspirin which we prepared by 1% ferric chloride and 1 ml ethanol we
    gat the color a little bit darken than the commercial aspirin color.

    Test Tube Color


    Salicylic Acid (#1) Blue black
    Commercial Aspirin (#2) Orange
    Prepared Aspirin (#3) Darken orange

    And the solubility of prepared aspirin in solution of


    Distilled water :low soluble or in soluble
    Sodium bi carbonate: it is soluble
    Ethanol: it is soluble
    CONCLUSION:
    From the above experiment we have concluded that the 3 taste
    tubes have different solubility rate in which the aspirin dissolved
    quickly the 3 taste tubes also presented different color as well as
    intensity. One thing we observed different from theoretical point
    of view is that the commercial aspirin didn’t dissolve quicker than
    our prepared aspirin

    Calculating the percent Yield of Aspirin

    Weigh the aspirin and calculate the theoretical (maximum) yield. [Note: The
    acetic anhydride is in excess, and the salicylic acid is the limiting reagent. Use the
    salicylic acid to calculate the theoretical yield.
    C7H6O3+C4H6O3=C9H8O4+CH3COOH
    From the above reaction we know the amount of salicylic acid is a 1 to 1 (1:1)
    ratio with the amount of aspirin. This means every mole of salicylic acid used will
    yield the same number of moles of aspirin. Therefore, the first step is to calculate
    the number of moles of salicylic acid used. Note: acetic anyhydride is in excess
    and salicylic acid is the limiting reagent
    1. Mass of asipirin = 0.89 g
    2. Molar mass of asipirin = 180.15 g/moles
    3. Moles of asipirin = 0.89/180.15 = 0.004940 moles
    1. Mass of acetic anhydride = 2.7 g
    2. Molar mass of acetic anhydride = 102.04 g/moles
    3. Moles of acetic anhydride = 2.7/102.04 = 0.0264602 moles
    1. Mass of Salicylic Acid Used (mock value) = 1.0 g
    2. Molar Mass of Salicylic Acid = 138.12 g/moles
    3. Moles of Salicylic Acid = 1.0/138.12 = 0.00724 moles
    1. Moles of Salicylic Acid = Moles of Aspirin —> 0.00724 moles of
    Salicylic Acid makes 0.00724 moles of Asprin
    2. Molar Mass of Aspirin = 180.16 g/moles
    3. Theoretical yield of Aspirin (g) = (0.00724 moles)(molar mass
    of aspirin) = 0.00724(180.16) = 1.304373 grams
    Your actual yield will be the amount aspirin you weighed after it was
    filtered and dried in lab. Using the theoretical and actual you can
    calculate percent yield.

    1. Actual Yield of Aspirin in lab after filtered/dried (mock value) =


    0.82 g
    2. Mass of Theoretical Yield of Aspirin (mock value) = 1.304373
    g
    3. Percent Yield = (Actual ÷ Theoretical) x 100 = (0.82 ÷
    1.304373) x 100 = 62.86545 %

    Quiz Questions
    1. Why is the carboxyl group of salicylic acid not acetylated?
    2. The melting point of salicylic acid is 157-159°C while that of acetylsalicylic
    acid which has a higher molecular weight is around 135°C. Explain why?
    3. What is the rational for the observed color reaction between salicylic acid
    and ferric chloride?
    4. How can one use infrared spectra to distinguish the product of this product
    of this experiment from the starting materials.
    Answers
    1. phenol OH is more reactive towards acetic anhydride than acidic OH because
    charge density is distributed among two oxygen of carboxylic group (lower
    nucleophilicity)
    Because the product determine steps involves the attack of phenolic OH to the
    protonated anhydride and is directed by the greater nucleophilicity if phenolic OH
    rather than carboxylic OH.
    2. The difference is the absence of the -OH group on the benzene ring of
    the latter one, replaced with an acetyl group -OCOCH₃.This means
    aspirin is less capable of form hydrogen bonds with other -OH on
    adjacent molecules, being the acetyl group a less polar one. The
    stronger the intermolecular attractions among adjacent molecules, the
    more energy is required to take molecules apart in the solid and,
    therefore, the higher the melting point
    3. Ferric chloride is used as the test of enols. Since salicylic acid also contains
    an enolic functional group. So, when ferric chloride is treated with salicylic
    acid a violet color is observed.
    4. by knowing the functional groups present in the starting material and final
    product, they can be differentiated with the help of IR spectroscopy. They
    are often distinguished by the disappearance or appearance of stretches or a
    change in frequency of a vibrational mode.

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