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    Lab Report 6

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    Evelyn
    The document summarizes an experiment to synthesize p-nitroacetanilide through the nitration of acetanilide. Acetanilide was dissolved in sulfuric acid and treated with a mixture of nitric and sulfuric acids. This produced both the para and ortho isomers of nitroacetanilide. The major product was the para isomer due to steric hindrance. However, the isolated product was impure and yellow in color, rather than the expected pure white of the para isomer alone. The percent yield was calculated to be 333%, suggesting impurities were present in the final product.

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    Lab Report 6

    Uploaded by

    Evelyn
    122 views4 pages
    The document summarizes an experiment to synthesize p-nitroacetanilide through the nitration of acetanilide. Acetanilide was dissolved in sulfuric acid and treated with a mixture of nitric and sulfuric acids. This produced both the para and ortho isomers of nitroacetanilide. The major product was the para isomer due to steric hindrance. However, the isolated product was impure and yellow in color, rather than the expected pure white of the para isomer alone. The percent yield was calculated to be 333%, suggesting impurities were present in the final product.

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    The document summarizes an experiment to synthesize p-nitroacetanilide through the nitration of acetanilide. Acetanilide was dissolved in sulfuric acid and treated with a mixture of nitric and sulfuric acids. This produced both the para and ortho isomers of nitroacetanilide. The major product was the para isomer due to steric hindrance. However, the isolated product was impure and yellow in color, rather than the expected pure white of the para isomer alone. The percent yield was calculated to be 333%, suggesting impurities were present in the final product.

    Copyright:

    © All Rights Reserved
    Download as DOC, PDF, TXT or read online from Scribd
    Download as doc, pdf, or txt
    122 views4 pages

    Lab Report 6

    Uploaded by

    Evelyn
    The document summarizes an experiment to synthesize p-nitroacetanilide through the nitration of acetanilide. Acetanilide was dissolved in sulfuric acid and treated with a mixture of nitric and sulfuric acids. This produced both the para and ortho isomers of nitroacetanilide. The major product was the para isomer due to steric hindrance. However, the isolated product was impure and yellow in color, rather than the expected pure white of the para isomer alone. The percent yield was calculated to be 333%, suggesting impurities were present in the final product.

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    © All Rights Reserved
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    of 4

    Lab Seven Synthesis of p-nitroacetanilide Evelyn Lupancu

    11/03/19
    I. Abstract
    In this experiment p-nitroacetanilide was prepared from acetanilide by nitration, forming in the
    para position as a major product. The para-substituted derivative was then isolated from the
    ortho-substituted derivative. The yield of the product was calculated as 333%.

    II. Introduction
    Nitration is an important reaction which is used in the preparation of nitro compounds. Nitro
    compounds, such as nitroacetanilide, are used as starting materials for many important
    commercially useful materials such as dyes, drugs, explosives, etc. In this experiment, p-
    nitroacetanilide was prepared by nitration of acetanilide. In nitration, the nitronium ion acts as
    the electrophile that involves the attack of the electron-rich benzene ring. The acetamido group (-
    NHCOCH3) in acetanilide is ortho and para directing, due to the resonance delocalizing the
    benzene ring by nitrogen lone pair. Therefore, on nitration a mixture of the two products is
    formed. Due to the bulky acetamido group, steric hindrance occurs at the ortho position. Thus,
    the major product is p-nitroacetanilide. In theory, during crystallization, the p-nitroacetanilide is
    isolated from any remaining o-nitroacetanilide and acid, yielding a white product.

    III. Experimental
    Approximately 7 mL of concentrated sulfuric acid was placed in a 125 mL flask and cooled in an
    ice bath. 3.4 grams of acetanilide was added to the flask in small increments with swirling until it
    dissolved. In a graduated cylinder 3 mL of concentrated sulfuric acid and 3 mL of concentrated
    nitric acid was mixed and cooled in an ice bath. The cold acid mixture was added, drop by drop,
    over a period of 5 minutes to the acetanilide-sulfuric acid mixture. The mixture stood at room
    temperature for an additional ten minutes, occasional swirled. Instead of pouring the mixture
    over 30 grams of crushed ice in a 150 mL beaker, 150 mL of cold water was used in its place to
    save time. The resulting solid was collected by suction filtration and rinsed several times with
    cold water to remove all the acid. The product was washed twice with 5 mL of methanol to
    further dehydrate the product. The dry product was weighed and a percent yield was then
    determined.

    IV. Results
    1. Limiting reagent: Acetanilide
    2. Theoretical yield of p-nitroacetanilide: 4.5 grams
    3. Actual yield of p-nitroacetanilide: 15 grams
    4. 5. Percent yield: 333%
    5. Properties of Reagents Used

    Reagent mmoles MW (g/mol) Mass (g) V (mL) D (g/mL)

    Acetanilide 0.025 135.17 3.4 - 1.22

    HNO3 0.068 63.01 - 3 1.42

    H2SO4 0.056 98.08 - 3 1.84

    A description of the calculations can be found in the Appendix

    V. Discussion
    The extremely high percent yield obtained for the dry product could be due to water that did not
    leave during the crystallization and dehydration process, or other impurities. The expected
    product of p-nitroacetanilide is known to be white, and the product that was formed was much
    more yellow. Thus, it can be implied that the final product did not consist of only nitroacetanilide
    in the para position. There could be impurities in the product, such as ortho and meta directing
    substances. The ortho position is what caused the yellow color, thus adding to the high percent
    yield. In principle, only para-nitration should occur due to the cooler temperatures used in the
    experiment. Additionally, para-nitration would occur due to steric hindrances at the ortho group.
    Higher temperatures would result in more ortho directing substances, thus any occurrence during
    the experiment that would expose the product to heat would lead to less para directing
    substances. For example, the flask containing the sulfuric acid/acetanilide mixture heated up
    during the experiment, which could have been prevented had it been placed in an ice bath.
    Because the addition of nitric acid is exothermic, the mixture would get too hot exceeding the
    temperature range suitable for the nitration. To avoid this, the addition of HNO3 should be done
    very slowly, dropwisely. Other impurities in the product could have included traces of acid,
    should be removed because hydrogen ions catalyze the hydrolysis of the amide to p-nitroaniline.
    In theory, acid was removed by pouring the mixture onto ice and water and filtering. It was
    necessary to mask the amino group before nitration in order to lead to the nitroacetanilide
    product. If aniline reacted with HNO3 in sulfuric acid, the amino group would have become
    ammonia. Thus, in order to counteract this, acetic anhydride and acetic acid is added to aniline,
    creating acetanilide and acetic acid products.

    The solubility of acetanilide:

    Mechanism of the nitration


    of acetanilide in concentrated sulfuric acid:

    Meta-directing: Para-directing: Ortho-directing:

    VI. Conclusions
    Percent yield of p-nitroacetanilide: 333%
    Mass of product: 15 g
    Theoretical mass: 4.5 g
    VII. References
    “Principles of Organic Chemistry 2” CHEM - 2425 Laboratory Manual

    VIII. Appendix
    Calculating Theoretical Yield of p-nitroacetanilide:
    Moles acetanilide= 3.4 g acetanilide x 1 mol/ 135.17 g = 0.025 mol acetanilide
    Moles HNO3 = 3 mL HNO3 x 1.42 g/1 mL x 1 mole/63.01 g = 0.068 mol HNO3
    Moles H2SO4 = 3 mL H2SO4 x 1.84 g/1 mL x 1 mole/98.08 g = 0.056

    **Acetanilide is limiting reagent**

    0.025 mol acetanilide x 1 mol p-nitroacetanilide/ 1 mol acetanilide x 1 mol p-nitroacetanilide /


    180.16 g = 4.5 g p-nitroacetanilide (Theoretical)

    Percent Yield:
    15 g (actual) / 4.5 g (expected) x 100 = 333% yield p-nitroacetanilide

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