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    Practice Problems Set 1 (CHM-614)

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    Practice Problems Set 1 (CHM-614)

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    sundasshoaib025
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    1 views2 pages

    Practice Problems Set 1 (CHM-614)

    Uploaded by

    sundasshoaib025

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    Course Instructor: Dr. Syed M.

    Saad

    THE CHEMISTRY OF RADICALS

    Practice Problems Set 1:

    1. Order the following molecules according to their rate of radical formation (slowest to fastest).

    2. Rank the following radicals in order of their stability (least stable to most stable).

    3. In addition to more highly chlorinated products, chlorination of butane yields a mixture of compounds with the
    formula C4H9Cl.

    a. Taking stereochemistry into account, how many different isomers with the formula C4H9Cl would you expect?

    b. If the mixture of C4H9Cl isomers were subjected to fractional distillation (or gas chromatography), how many
    fractions (or peaks) would you expect?

    c. Which fractions would be optically inactive?

    d. Which fractions could theoretically be resolved into enantiomers?

    e. Predict features in the 1H and 13C DEPT NMR spectra for each that would differentiate among the isomers
    separated by distillation or gas chromatography.

    f. How could fragmentation in their mass spectra be used to differentiate the isomers?

    1
    Course Instructor: Dr. Syed M. Saad

    4. On reacting 2-methylbutane with one equivalent Cl2, four different monochloro isomers are obtained.

    Calculate the percentage of each isomer. The reactivity of the C−H bond varies from tertiary > secondary > primary
    by the ratio 5:4:1.

    5. Di-tert-butylperoxide (CH3)3CO−OC(CH3)3 is a stable liquid at room temperature that easily forms free radicals
    upon heating. A mixture of 2-methylpropane and CCl4 is fairly stable at 130-140 °C. On addition of a small amount
    of di-tert-butylperoxide this mixture mainly reacts to form tert-butylchloride and chloroform. Tert-butyl-alcohol
    can also be isolated, twice as much as the amount of di-tert-butylperoxide added.

    Give the initiation step and the two propagation steps for this radical chain reaction.

    6. The termination of radical reactions proceeds by the recombination of two radicals.

    Provide the main product J and three possible termination products (K–M) of the following radical reaction.

    7. Write a radical chain mechanism for the following reaction (a reaction called the Hunsdiecker reaction).

    8. The halogen atom of an alkyl halide can be replaced by the hydrogen atom bonded to tin in tributyltin hydride
    (Bu3SnH). The process, called dehalogenation, is a radical reaction, and it can be initiated by AIBN (2,2′-
    azobisisobutyronitrile). AIBN decomposes to form nitrogen gas and two isobutyronitrile radicals, which initiate the
    reaction. Write a mechanism for the reaction.

    9. The bromination of o-xylene can be done either under light illumination or in the dark. The NMR spectrum of F in
    the aliphatic region shows a singlet at 4.56 ppm, while that of G shows a singlet at 4.56 ppm and a singlet at 2.29
    ppm. The molecular mass of F is larger than that of G, as determined by mass spectrometry.

    Provide the structures of the two main products in both reactions (F/G and H/I).

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