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    Chem 31.1 Exp 8 and 9

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    Dean Dela Cruz
    1. The document summarizes the results of two experiments involving organic reactions with bromine. It lists the equations for reactions that tested positive and whether they were substitution or addition. 2. It explains that steam distillation is used to extract limonene because it allows extraction at lower temperatures to avoid dissolving the compound. 3. It provides order of reactivity for compounds towards bromine based on electron donating/withdrawing groups and explains that experimental results did not fully agree with theory due to possible errors.

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    Chem 31.1 Exp 8 and 9

    Uploaded by

    Dean Dela Cruz
    536 views2 pages
    1. The document summarizes the results of two experiments involving organic reactions with bromine. It lists the equations for reactions that tested positive and whether they were substitution or addition. 2. It explains that steam distillation is used to extract limonene because it allows extraction at lower temperatures to avoid dissolving the compound. 3. It provides order of reactivity for compounds towards bromine based on electron donating/withdrawing groups and explains that experimental results did not fully agree with theory due to possible errors.

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    1. The document summarizes the results of two experiments involving organic reactions with bromine. It lists the equations for reactions that tested positive and whether they were substitution or addition. 2. It explains that steam distillation is used to extract limonene because it allows extraction at lower temperatures to avoid dissolving the compound. 3. It provides order of reactivity for compounds towards bromine based on electron donating/withdrawing groups and explains that experimental results did not fully agree with theory due to possible errors.

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    536 views2 pages

    Chem 31.1 Exp 8 and 9

    Uploaded by

    Dean Dela Cruz
    1. The document summarizes the results of two experiments involving organic reactions with bromine. It lists the equations for reactions that tested positive and whether they were substitution or addition. 2. It explains that steam distillation is used to extract limonene because it allows extraction at lower temperatures to avoid dissolving the compound. 3. It provides order of reactivity for compounds towards bromine based on electron donating/withdrawing groups and explains that experimental results did not fully agree with theory due to possible errors.

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    You are on page 1of 2

    Collin Jeremiah R.

    Balayan
    2013 - 14713
    Experiment 8
    to Questions

    Answers

    1. Write the equations for all the tests giving positive results. Classify whether each
    of the reactions is a substitution or an addition reaction.

    t-BuCl + AlCl3 -> t-Bu+ + AlCl4- ---- benzene --->

    Limonene + Br2 (in light) ->

    Addition

    Substitution

    Benzene + Br2 -> HBr +


    Addition
    3C10H16 + 4KMnO4 + 8H2O -> 3C10H24O4 + 4MnO2 + 4KOH
    2 Hexane + O2 -> 12CO2 + 14H2O
    2 Limonene + O2 -> 20 CO2 + 6H2O
    2 Benzene + O2 -> 12 CO2 + 6 H2O
    2. What are the advantages of using steam distillation in extracting limonene?
    Steam distillation is used to extract compounds like limonene that are
    temperature sensitive. Natural aromatic compounds like limonene dissolve in high
    temperatures. The steam carries vaporized limonene that is then condensed and
    separated with water because they are immiscible. This allows limonene to be
    extracted at lower temperature compared to other distillation techniques so that it
    will not dissolve.
    Source: Organic Chemistry by Solomons

    Collin Jeremiah R. Balayan


    2013 - 14713
    Experiment 9
    to Questions

    Answers

    1. Arrange the compounds used in the experiment in order of increasing reactivity


    towards Br2 in CH3COOH. Explain
    chlorobenzene -> benzene-> nitrophenol -> acetinilide -> phenol -> aniline
    These compounds are arranged based on the properties of the groups
    connected to the benzene ring. The trend is that the stronger the electron donating
    group, the more reactive the compound and the stronger the electron withdrawing
    group, the less reactive the compound.
    2. Do your experimental results agree with the theoretical data? If not, what are the
    possible sources of error?
    The results did not match the theoretical data. Sources of error can include
    false positives, lack of definitive endpoint and wrong start of timing the reactions.
    3. Predict the order of reactivity of the following compounds towards chlorination
    from the least reactive to the most reactive:
    A. Toluene, nitrobenzene, anisole and methylbenzoate
    nitrobenzene -> methylbenzoate -> toluene -> anisole
    B. benzene, acetophenone, bromobenzene and benzyl alcohol
    acetophenone -> bromobenzene -> benzene -> benzyl alcohol
    C. styrene, benzaldehyde, aniline and iodobenzene
    benzaldehyde -> Iodobenzene -> styrene -> aniline
    4. Explain the effect of solvent in the reaction of acetanilide and Br2 in part B.
    A more polar solvent can induce a stronger dipole in the Br 2 molecule to make
    it more electrophilic so that it takes smaller activation energy for the reaction to
    occur.
    Source: Organic Chemistry by Solomons

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