Location via proxy:   [ UP ]  
[Report a bug]   [Manage cookies]                
Scribd Logo
Upload

Welcome to Scribd!

  • 220 views

    Chem31.1 ATQ9 Santos PDF

    Uploaded by

    Claire Santos
    1. The document discusses an experiment on the relative rates of electrophilic aromatic substitution. It provides the order of reactivity of compounds towards bromine from most to least reactive based on their substituents. 2. There was a slight discrepancy between the theoretical predictions and experimental results, which may have been due to errors in the experiment such as contaminated chemicals or inappropriate proportions. 3. The order of reactivity of compounds towards chlorination from least to most reactive is predicted for several sets of compounds based on their substituents. 4. Acetic acid is a better solvent than cyclohexane for the bromination of toluene because it is a Lewis acid that forms a complex with brom

    Copyright:

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

    Chem31.1 ATQ9 Santos PDF

    Uploaded by

    Claire Santos
    220 views2 pages
    1. The document discusses an experiment on the relative rates of electrophilic aromatic substitution. It provides the order of reactivity of compounds towards bromine from most to least reactive based on their substituents. 2. There was a slight discrepancy between the theoretical predictions and experimental results, which may have been due to errors in the experiment such as contaminated chemicals or inappropriate proportions. 3. The order of reactivity of compounds towards chlorination from least to most reactive is predicted for several sets of compounds based on their substituents. 4. Acetic acid is a better solvent than cyclohexane for the bromination of toluene because it is a Lewis acid that forms a complex with brom

    Original Title

    Chem31.1_ATQ9_Santos.pdf

    Copyright

    © © All Rights Reserved

    Available Formats

    PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    1. The document discusses an experiment on the relative rates of electrophilic aromatic substitution. It provides the order of reactivity of compounds towards bromine from most to least reactive based on their substituents. 2. There was a slight discrepancy between the theoretical predictions and experimental results, which may have been due to errors in the experiment such as contaminated chemicals or inappropriate proportions. 3. The order of reactivity of compounds towards chlorination from least to most reactive is predicted for several sets of compounds based on their substituents. 4. Acetic acid is a better solvent than cyclohexane for the bromination of toluene because it is a Lewis acid that forms a complex with brom

    Copyright:

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

    Chem31.1 ATQ9 Santos PDF

    Uploaded by

    Claire Santos
    1. The document discusses an experiment on the relative rates of electrophilic aromatic substitution. It provides the order of reactivity of compounds towards bromine from most to least reactive based on their substituents. 2. There was a slight discrepancy between the theoretical predictions and experimental results, which may have been due to errors in the experiment such as contaminated chemicals or inappropriate proportions. 3. The order of reactivity of compounds towards chlorination from least to most reactive is predicted for several sets of compounds based on their substituents. 4. Acetic acid is a better solvent than cyclohexane for the bromination of toluene because it is a Lewis acid that forms a complex with brom

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 2

    Santos, Clarice March 6, 2019

    EXPERIMENT 9: RELATIVE RATES OF ELECTROPHILIC AROMATIC SUBSTITUTION


    ANSWER TO QUESTIONS

    1. Arrange the compounds used in the experiment in order of increasing reactivity towards
    Br2 in CH3COOH. Explain.
    The reactivity of a compound with an aromatic ring depends on the nature of its
    substituent/s, wheter it is an electron-donating or electron-withdrawing from the ring.
    Electron-withdrawing group (EWG) makes the ring less reactive towards an electrophile
    like bromine while electron-donating groups (EDG) amkes it more reactive because it
    increases the electron density of the aromatic ring. For that reason, we can arrange the
    substituents from fastest to slowest reactivity as follows: -CH3 > amino(-NH2) > hydroxyl
    (-OH) > acylamino (-NHCOR) > hydrogen (-H) > halogen (-X) > nitro (-NO2).

    Therefore, we can also arrange the following compounds into: toluene > phenol >
    chlorophenol > benzaldehyde > nitrophenol.

    2. Do the experimental results agree with the theoretical data? If not, what are the possible
    sources of error?
    There is a slight discrepancy between the theoretical data and experimental
    results. Since the experiment was qualitative, errors were possibly committed during the
    experiment like: contaminated chemical reagents, inappropriate proportions, environmental
    factors such as temperature and light, human errors, etc.

    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< anisole < toluene

    B. benzene, acetophenone, bromobenzene, and benzyl alcohol


    acetophene < bromobenzene < benzene < benzene

    C. styrene, benzaldehyde, aniline, and iodobenzene


    benzaldehyde < iodobenzene < styrene < aniline

    4. Explain the effect of solvent in the reaction of toluene and Br2 in Part B.
    Bromination of toluene was faster in acetic acid than in cyclohexane. Acetic acid
    is a Lewis acid - it is an electron-pair acceptor. As a catalyst, the reaction of aromatic
    compounds with halogen will undergo substitution since the Lewis acid will form a
    complex with the halogen leaving the aromatic ring intact. On the other hand,
    cyclohexane is nonpolar causing it to be less reactive that causes slower reaction.

    References:
    Carey, F. A. (2006). Organic Chemistry 6th ed. Chapter 12: Reactions of Arenes:
    Electrophilic Aromatic Substitution. McGraw-Hill: New York. pp. 496-512.
    McMurry, J. (2015). Organic Chemistry 9th ed. Chapter 16: Electrophilic Aromatic
    Substitution. Brooks/Cole, Cengage Learning: Belmont, pp. 479-514.
    Organic Chemistry Laboratory Manual

    Name: Clarice Santos_________________


    Groupmate: Alpecho, Tiampong_________ Date Performed: _03.22.2019_________
    Section: _WFR____________________

    EXPERIMENT 9. RELATIVE RATES OF ELECTROPHILIC AROMATIC SUBSTITUTION

    A. Relative Rates of Bromination

    Test Compound Structure Time of decolorization

    Benzaldehyde fast

    Chlorophenol slow

    Phenol fast

    Nitrophenol fast

    Toluene immediate

    B. Effect of Solvents on Reaction Rates

    Solvent Time of decolorization

    Cyclohexane 5 minutes
    Acetic acid immediate

    You might also like