l>Chem2OB3 - Experiment 1b - Isolation of (+)- and (-)-Carvone
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Experiment 1b. Isolation of essential Oils by Preparative GasChromatography

In this experiment, us isolate (+)-carvone native caraway seed oil or (-)-carvone fromspearmint oil, utilizing preparative gas chromatography. (+)- and (-)-carvone are enantiomers,and their odors space distinctly different from each other. This is to be expected, sincethe human being body distinguishes odor by the communication of molecules v odor receptors inthe nose, which room chiral. The phenomenon in i beg your pardon a chiral receptor interactsdifferently v each the the enantiomers of a chiral compound is dubbed chiralrecognition. One more example that chiral recognition have the right to be found in the toxicityof the 2 carvone isomers; the toxicity that (+)-carvone in rats is 400 times better thanthat that (-)-carvone.

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With the exemption of their optical rotations, the physics properties that enantiomersare identical. Thus, we predict the the boiling points, refractive indices, gaschromatographic retention times, infrared and nuclear magnetic resonance spectra of (+)-and (-)-carvone must all be identical. The only distinction in properties that one shouldobserve space the odors and the indications of optical rotation in a polarimeter.

Caraway seed oil contains mainly limonene and (+)-carvone. The(+)-carvone (bp 230 oC) can easily be separated from the lower-boiling limonene(bp 177 oC) by gas chromatography, as depicted in theGC-traces shown below in number 1. Utilizing gas repertoire tubes, the two significant components ofthe organic oil have the right to be gathered separately as they elute indigenous the column. Spearmintoil contains mainly (-)-carvone, v a smaller amount of limonene and theisomeric terpenes, a- and also b-phellandrene.The gas chromatogram of this oil is additionally shown in number 1. In this case, while that is easyto collect a pure sample of the carvone, limonene cannot be gathered in pure form becauseit will be contaminated through the various other terpenes, which have comparable boiling points.


Your instructor will either assign you spearnintor caraway oil, or have actually you choose one the the oils. You will likewise be given instructions onwhich optional procedures, if any, you space to perform. Your instructor may have youisolate both the carvone and limonene components or only carvone. Avoid call with(+)-carvone, together it is really toxic.

Gas Chromatography

In this experiment, you will bring out all aspects of the gaschromatographic separation yourself. The most critical part the the operation is the injectionprocedure - the is essential that as soon as you have pierced the injector with the syringecontaining the mixture to be separated, girlfriend inject the mixture rapidly. Your T.A. Willdemonstrate the exactly procedure for you; exercise on your very own several times through thesmall containers listed in the GC room, utilizing the ethanol services provided, till youare confident that you deserve to do the properly.

Inject 50-mL of caraway-seed or spearmint oil ~ above the gas color layer analyzer column. Justbefore a component of the oil (limonene or carvone) elutes native the column, install a gascollection tube at the exit port. To determine when to connect the gas collection tube,refer come the chromatograms on the wall surface of the GC room. This chromatograms have actually been runon the same instrument you are using under the exact same conditions. Ideally, girlfriend shouldconnect the gas collection tube just before the limonene or carvone elutes indigenous the columnand eliminate the pipe as quickly as every the component has been collected, yet before any type of othercompound begins to elute from the column. This can be completed most easily by watchingthe recorder together your sample passes v the column. The collection tube is connected(if possible) just prior to a optimal is produced, or as quickly as a deflection in the pen isobserved. Once the pen has actually returned to the basic line, the gas collection tube is removed.

This procedure is reasonably easy for collecting the carvone component of both oils andfor collecting limonene in caraway-seed oil. Since of the existence of number of terpenesin spearmint oil, it is somewhat more challenging to isolation a pure sample that limonene fromspearmint oil (see chromatogram in figure). In this case, girlfriend must try to collect just thelimonene component and not any other compounds, such as the terpene i m sorry produces ashoulder ~ above the limonene optimal in the chromatogram for spearmint oil.

After collecting the samples, insert the ground joint of the repertoire tube right into a 0.1mL conical vial, making use of an O-ring and also cap to fasten the two pieces with each other securely.Insert the peak of the collection tube v the hole in the rubber septum cap and also placethis assembly right into a centrifuge tube. Put cotton top top the bottom the the pipe to preventbreakage. Balance the centrifuge by put a pipe of equal weight on the opposite side.During centrifugation, the sample is required into the bottom the the conical vial.

Disassemble the apparatus, cap the vial, and also perform the analyses described below.


The samples derived by gas chromatography and also centrifugation must be analyzed by themethods below. To compare your results with those obtained by who who offered a differentoil. In addition, measure up the optical rotations that the advertisement samples that (+)-carvoneand (-)-carvone.

Gas Chromatography. Determine the retention times of the components. Calculate thepercentage composition of the carvone sample by the triangulation method. In thismethod, a GC height is approximated as a triangle, the area of which is proportional come theamount of material detected. The area the the top is approximately equal to � X (peakheight) X (peak broad at half-height).

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Infrared Spectroscopy. Obtain the infrared spectrum of the (-)-carvone sample fromspearmint or the the (+)-carvone sample indigenous caraway. Also obtain the infrared spectrum ofthe (+)-limonene, i m sorry is found in both oils. Determine both spectra on succinct samples. If absolutelynecessary, you may include one fall of nujol to the sample and mix it thoroughlybefore running the spectrum. The spectrum will contain extra C-H absorptions ataround 3000 cm-1, however, together nujol (a.k.a. Mineral oil) is a mixture of longchain aliphatic hydrocarbons.

Polarimetry. With the assist of the T.A., measure up the optical rotation the the(+)-carvone and (-)-carvone samples provided. Calculate the certain rotation that eachcompound (B&F, pp. 140-142). The concentration c will equal the thickness of thesubstances anaiyzed in ~ 20 oC. The values are 0.9608 g/mL for (+)-carvone and0.9593 g/mL because that (-)-carvone. The literary works values for the certain rotations room asfollows: