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    Experiment 2: Reduction of Camphor To Isoborneol

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    Dona
    This experiment reduced camphor to isoborneol through sodium borohydride. The theoretical yield was 0.2634g and actual yield was 0.240g, giving a 91.11% percent yield. Infrared spectroscopy could detect the carbonyl in camphor but not in isoborneol. The gem-dimethyl peaks were more distinct in isoborneol NMR due to the equatorial hydroxyl groups. An isoborneol sample still showing a carbonyl band indicated an incomplete reduction of camphor.

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    Experiment 2: Reduction of Camphor To Isoborneol

    Uploaded by

    Dona
    139 views2 pages
    This experiment reduced camphor to isoborneol through sodium borohydride. The theoretical yield was 0.2634g and actual yield was 0.240g, giving a 91.11% percent yield. Infrared spectroscopy could detect the carbonyl in camphor but not in isoborneol. The gem-dimethyl peaks were more distinct in isoborneol NMR due to the equatorial hydroxyl groups. An isoborneol sample still showing a carbonyl band indicated an incomplete reduction of camphor.

    Original Description:

    Detailed experiment observations of the reduction of camphor to isoborneol

    Original Title

    Experiment 2

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    This experiment reduced camphor to isoborneol through sodium borohydride. The theoretical yield was 0.2634g and actual yield was 0.240g, giving a 91.11% percent yield. Infrared spectroscopy could detect the carbonyl in camphor but not in isoborneol. The gem-dimethyl peaks were more distinct in isoborneol NMR due to the equatorial hydroxyl groups. An isoborneol sample still showing a carbonyl band indicated an incomplete reduction of camphor.

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

    Experiment 2: Reduction of Camphor To Isoborneol

    Uploaded by

    Dona
    This experiment reduced camphor to isoborneol through sodium borohydride. The theoretical yield was 0.2634g and actual yield was 0.240g, giving a 91.11% percent yield. Infrared spectroscopy could detect the carbonyl in camphor but not in isoborneol. The gem-dimethyl peaks were more distinct in isoborneol NMR due to the equatorial hydroxyl groups. An isoborneol sample still showing a carbonyl band indicated an incomplete reduction of camphor.

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    © All Rights Reserved
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    of 2

    Experiment 2: Reduction of Camphor to Isoborneol

    Abstract:
    In this lab, the reduction of the carbonyl group via sodium borohydride was investigated.
    Through this process camphor is reduced to isoborneol an isomeric alcohol. A mixture of
    camphor, methanol, sodium borohydride was boiled and filtered through a Hirsch funnel,
    assisted with methylene chloride. After drying the solvent was evaporated leaving the product
    isoborneol. The theoretical yield was 0.2634g and the actual yield was 0.240g. The overall
    percent yield was 91.11%. The melting point was not measured for this experiment but the actual
    yield for isoborneol is 212C.

    Observations:
    1. With the addition of sodium borohydride, the mixture of camphor and methanol began to
    bubble and emitted heat. This is indicative of a reaction taking place.
    2. During the filtration process, a white solid product was retrieved. This product was
    similar to our initial camphor product.
    3. After the addition of the ice water the solution turned a cloudy white color. Again this is
    indicative of a reaction taking place.

    Results-Data
    Mass of Erlenmeyer flask: 41.68g
    Mass of camphor: 0.26g
    Mass of sodium borohydride: 0.25g
    Theoretical yield: 0.2634g
    Actual yield: 0.240g
    Percent Yield: 91.11%
    Actual melting point: 212C
    Explanation of Results
    The percent yield for this experiment was 91.11%. The melting point was not measured for this
    experiment as the actual melting point temperature of isoborneol is very high. However,
    isoborneol is assumed to be the collected product as this product would be more favored over the
    other products that may be hindered sterically. The actual yield is quite close to the theoretical
    yield. However, the small discrepancy could be due to a loss of product during filtration as it was
    discovered there was a small break in the filtration paper.

    Conclusion:
    In conclusion, this experiment in the reduction of camphor to isoborenol can be considered a
    success. This experiment could be made better through a melting point analysis so there is no
    need to assume the collected product is isoboreneol. However, this assumption can be justified as
    the production of borneol is restricted due to the steric hindrance on the camphor.

    Post- Lab Questions:


    1. Interpret the major absorption bands in the infrared spectra of camphor, borneol, and
    isoborneol.
    a. For camphor the largest signal is at ~1750. This is representative of carbonyl, C to
    O double bonds. For both isoborenol and borneol there are deep peaks at ~3000
    and ~3400, however, borneol’s ~3400 peak was larger due to its axial and
    substituent group position. Isoboreeol’s transmittance is lower due to its
    functional groups being in the equatorial position.
    2. Explain why the gem-dimethyl appear as separate peaks in the proton- NMR spectrum of
    isoborneol, although they almost overlap in borneol.
    a. The germinal groups are more distinct in the isoborenol because of the equatorial
    hydroxyl groups. These groups cause the methyl groups to have unique signals. In
    borneol, the alcohol is downward and doesn’t cause this effect.
    3. A sample of isoborneol prepared by reduction of camphor was analyzed by infrared
    spectroscopy and showed a band at 1750cm-1. This result is unexpected why?
    a. A band of 1750 is indicative of a carbonyl group as indicated by infrared spectra
    of camphor. Because the structure of isoborneol doesn’t feature a C=O this
    infrared spectra indicates that camphor wasn’t reduced properly. If it were to be
    reduced properly, the infrared spectra should have a band at O-H in the >3000
    range.

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