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    Relative Rates of Electrophilic Aromatic Substitution

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    This document summarizes an experiment on the relative rates of electrophilic aromatic substitution. It provides answers to questions about arranging compounds by reactivity based on their substituents, whether experimental results agreed with theoretical predictions, predicting reactivity order for different compounds, and explaining the effect of solvent. The key findings are that electron donating groups make compounds more reactive by increasing electron density, and the solvent can increase or decrease reaction rates by donating or withdrawing electrons from the aromatic ring.

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    Relative Rates of Electrophilic Aromatic Substitution

    Uploaded by

    Anonymous GO6JVW9Wud
    2K views2 pages
    This document summarizes an experiment on the relative rates of electrophilic aromatic substitution. It provides answers to questions about arranging compounds by reactivity based on their substituents, whether experimental results agreed with theoretical predictions, predicting reactivity order for different compounds, and explaining the effect of solvent. The key findings are that electron donating groups make compounds more reactive by increasing electron density, and the solvent can increase or decrease reaction rates by donating or withdrawing electrons from the aromatic ring.

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    Chem 31.1 Experiment 9 ATQ

    Original Title

    RELATIVE RATES OF ELECTROPHILIC AROMATIC SUBSTITUTION

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    This document summarizes an experiment on the relative rates of electrophilic aromatic substitution. It provides answers to questions about arranging compounds by reactivity based on their substituents, whether experimental results agreed with theoretical predictions, predicting reactivity order for different compounds, and explaining the effect of solvent. The key findings are that electron donating groups make compounds more reactive by increasing electron density, and the solvent can increase or decrease reaction rates by donating or withdrawing electrons from the aromatic ring.

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    © All Rights Reserved
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    Download as docx, pdf, or txt
    2K views2 pages

    Relative Rates of Electrophilic Aromatic Substitution

    Uploaded by

    Anonymous GO6JVW9Wud
    This document summarizes an experiment on the relative rates of electrophilic aromatic substitution. It provides answers to questions about arranging compounds by reactivity based on their substituents, whether experimental results agreed with theoretical predictions, predicting reactivity order for different compounds, and explaining the effect of solvent. The key findings are that electron donating groups make compounds more reactive by increasing electron density, and the solvent can increase or decrease reaction rates by donating or withdrawing electrons from the aromatic ring.

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    of 2

    RELATIVE

    RATES

    OF

    ELECTROPHILIC

    AROMATIC

    SUBSTITUTION
    J. V. DE GUZMAN
    DEPARTMENT OF CHEMICAL ENGINEERING, COLLEGE OF ENGINEERING
    UNIVERSITY OF THE PHILIPPINES, DILIMAN QUEZON CITY, PHILIPPINES
    DATE PERFORMED: MARCH 4, 2015
    INSTRUCTORS NAME: ALLAN KENNETH REGUNTON

    Answers to Questions:
    1. Arrange the compounds used in the experiment in order of increasing
    reactivity towards Br2 in CH3COOH. Explain.
    Shown below are the structures of these compounds:

    The reactivity of a compound with aromatic ring depends on the


    substituent/s. If the substituent is an electron withdrawing group also called
    deactivating group, it tends to withdraw the electron density from the ring,
    making the compound less reactive toward an electrophile like bromine. On
    the other hand, an electron donating group or an activating group increases
    the electron density of the aromatic ring making it more reactive towards an
    electrophile. Amine has an amino group while acetanilide has acylamino
    group. Phenol has a hydroxyl group while chlorobenzene has a halogen
    group. Nitrophenol has a nitro group and hydroxyl group whereas benzene
    has hydrogens bonded only.
    If arranged in order of increasing ability to donate an electron:
    Nitro( -NO2)<Halogen (-X) <Hydrogen (-H) <acylamino (-NHCOR) <hydroxyl (OH) <amino (-NH2)
    Therefore, it can be inferred that the compounds with the greatest ability to
    donate an electron are reactive toward the electrophilic bromine. As such, we
    can arrange the following compounds into:
    Nitrophenol< Chlorobenzene<benzene<acetanilide<Phenol<Aniline
    2. Do your experimental results agree with the theoretical data?
    No. There are apparent deviations from the data obtained. Results for aniline
    shows a very large time elapsed for the reaction when in fact it should be the
    most reactive. Possible reasons for these deviations include personal errors in
    distinguishing a positive result for a reaction. Since the test is qualitative
    only, few amounts of reagents are only used making the reaction and
    chemical change difficult to observe. Personal errors in obtaining the time for
    each reaction can also be a reason. On the other hand, it is also difficult to
    not expose the solution from sunlight since it is difficult to add the reagents in

    the dark. As such, when the solution is initially exposed by sunlight, free
    radical formation may have occurred therefore impeding the desired reaction
    to happen.
    3. Predict the order of reactivity of the following compounds towards
    chlorination from the least reactive to the most reactive.
    A. Toluene, nitrobenzene, anisole, methylbenzoate

    Substituent (increasing ability to donate an electron)


    Nitro (-NO2) < alkyl < acyloxy <alkoxy
    Nitrobenzene< toluene< methylbenzoate<anisole
    B. Benzene, acetophenone, bromobenzene and benzyl alcohol

    Acyl<halogen<H<-CH2-OH
    Acetophenone<bromobenzene<benzene<benzyl alcohol
    C. Styrene, benzaldehyde, aniline and iodobenzene

    Formyl<halogen<alkenyl<amine
    Benzaldehyde<iodobenzene<styrene<aniline
    4. Explain the effect of solvent in the reaction of acetanilide and Br 2 in part B.
    Acetic acid can also become a Lewis acid. It tends to donate electrons on the
    aromatic ring and thus make acetanilide more reactive towards bromination.
    On the other hand, cyclohexane tends to withdraw electrons from the group
    causing it to be less reactive. As predicted, it takes the reaction of bromine in
    cyclohexane with acetanilide longer than with acetic acid. As such, the
    solvent can increase the rate of the reaction by donating electrons to the
    aromatic ring or can decrease the rate by withdrawing electrons from the ring
    which is similar to what substituent groups do to the rate of reaction of an
    aromatic compound.
    References:
    [1] Carey, F. A. (2006). Organic Chemistry 6th ed. Chapter 12: Reactions of Arenes:
    Electrophilic Aromatic Substitution. McGraw-Hill: New York. pp. 496-512

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