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    Experiment 3 Expt 31B: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol

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    Constance Lu
    The document describes an experiment where camphor was reduced to isoborneol. Key details: - Camphor (0.25 g) was reduced with sodium borohydride (0.25 g) in methanol, forming a white solid of isoborneol. - The % yield of isoborneol was 74.2%, close to the theoretical yield. - Infrared spectroscopy showed borneol and isoborneol have an O-H stretching peak, while camphor has a C=O carbonyl peak, indicating reduction of the carbonyl group.

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    Experiment 3 Expt 31B: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol

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    Constance Lu
    780 views4 pages
    The document describes an experiment where camphor was reduced to isoborneol. Key details: - Camphor (0.25 g) was reduced with sodium borohydride (0.25 g) in methanol, forming a white solid of isoborneol. - The % yield of isoborneol was 74.2%, close to the theoretical yield. - Infrared spectroscopy showed borneol and isoborneol have an O-H stretching peak, while camphor has a C=O carbonyl peak, indicating reduction of the carbonyl group.

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    Experiment 3 Expt 31B: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol

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    Experiment 3 Expt 31B: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol

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    The document describes an experiment where camphor was reduced to isoborneol. Key details: - Camphor (0.25 g) was reduced with sodium borohydride (0.25 g) in methanol, forming a white solid of isoborneol. - The % yield of isoborneol was 74.2%, close to the theoretical yield. - Infrared spectroscopy showed borneol and isoborneol have an O-H stretching peak, while camphor has a C=O carbonyl peak, indicating reduction of the carbonyl group.

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    780 views4 pages

    Experiment 3 Expt 31B: An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol

    Uploaded by

    Constance Lu
    The document describes an experiment where camphor was reduced to isoborneol. Key details: - Camphor (0.25 g) was reduced with sodium borohydride (0.25 g) in methanol, forming a white solid of isoborneol. - The % yield of isoborneol was 74.2%, close to the theoretical yield. - Infrared spectroscopy showed borneol and isoborneol have an O-H stretching peak, while camphor has a C=O carbonyl peak, indicating reduction of the carbonyl group.

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    of 4

    Experiment 3

    Expt 31B: An Oxidation-Reduction


    Scheme: Borneol, Camphor,
    Isoborneol

    XiaoYing Lu
    Date of Experiment: 9 September 2016
    CHEM 3522 Friday Lab
    Section FQ9
    Prof. Gail Horowitz

    POST-LAB REPORT
    XiaoYing Lu
    Lab 3: Camphor
    Redn
    9/9/2016
    Observations:
    1. The solution was not cloudy anymore when 0.5 g of granular
    anhydrous sodium sulfate was added to it. This is significant because it
    indicates that the product isoborneol is successfully isolated from
    solution.
    2. The white solid was formed after the 0.25 g of sodium borohydride was
    added to 0.25 g of camphor along with 1.5 mL methanol. This is
    significant because it indicates that the sodium borohydride
    successfully reduced the camphor to isoborneol.
    Data:
    Melting point: 206C - 207C
    Preweighed flask = 38.124 g
    Preweighed flask + product = 38.312 g
    Product weight (isoborneol) = 0.188 g
    0.25 g camphor + 0.25 g NaBH4 isoborneol
    0.25 g camphor x 152.23 g/ mol = 1.64 x 10^-3 mol
    0.25 g NaBH4 x 37.83 g/ mol = 6.60 x 10^-3 mol, so camphor is the limiting
    reagent
    Theoretical yield of product = 1.64 x 10^-3 mol x 1mol isoborneol

    = 0.2533 g
    % Yield = (actual yield/theoretical yield) * 100
    = (0.188/ 0.2533) * 100 = 74.2 %

    Post-lab Question:
    1. Interpret the major absorption bands in the infrared spectra of
    camphor, borneol, and isoborneol.

    The IR spectra for camphor is 1750-1800cm^-1 because of its sharp


    peak which indicates the present of its carbonyl functional group C=O
    stretching; The IR spectra for borneol and isoborneol is 3200 - 3600
    cm^-1 because of its board peak which indicates the reduction of its
    carbonyl group and the present of its alcohol O-H stretching
    2. Explain why the gem-dimethyl groups appear as separate peaks in the
    proton NMR
    spectrum of isoborneol while they are an unresolved singlet in borneol.
    Gem-dimethyl group refers to two methyl groups of the same carbon atom.

    The hydroxyl group of borneol is on the opposite side to the gem-dimethyl


    group, so it doesn't matter which methyl group is closer to the OH group; In
    Isoborneol, the OH group is on the same side to the gem-dimethyl group,
    now its matter which methyl group interacts more with the OH group.
    3. A sample of isoborneol prepared by reduction of camphor was analyzed by infrared
    spectroscopy and showed a band at 1780 cm-1. This result was unexpected. Why?
    If the IR of isoborneol was 1780 cm-1 which is as same as camphor, that indicates the present of
    carbonyl group C=O. This is unexpected because isoborneol has no carbonyl group. The present
    of carbonyl group means the camphor was not completely reduced to this isoborneol.
    4. The observed melting point of camphor is often low. Look up the molal freezing-pointdepression constant K for camphor and calculate the expected depression of the
    melting point of a quantity of camphor that contains 0.5 molal impurity. Hint: Look in
    a general chemistry book under freezing-point depression or colligative properties
    of solution.

    Tf = Kf mB; Tf = (39.7 C/molal) (0.5 molal) = 19.85 C.


    To- Tf = 19.85,
    179 - Tf = 19.85 while the melt point of pure camphor is 179 C; Therefore,
    Tf= 159C
    5.

    The peak assignments are shown on the carbon-13 NMR spectrum of

    camphor. Using
    these assgnments as a guide, assign as many peaks as possible in the
    carbon-13 spectra
    of borneol and isoborneol.

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