This organic layer was drained into the first organic layer.

The organic solution was dried

with anhydrous sodium sulfate, and this mixture was filtered by gravity filtration to yield a
water-free organic solution in a 150mL round bottom flask. This hexane solvent was evaporated
via rotary evaporation, leaving the eugenol oil behind in the flask. A sample of this oil was
prepared in dichloromethane so that it could be analyzed by gas chromatography, and the rest of
the oil was saved for IR analysis.
The gas chromatograph (Graph 1) shows that the sample is almost 100% eugenol, with
trace contamination of caryophellene, confirming efficient methods of separation and extraction.
This trace impurity could be due to residue left in the glassware that was not washed away after
the extractions.
A sample of the eugenol oil was analyzed by infrared spectroscopy (IR). The spectrum
(Graph 2) identifies functional groups present in the molecules in the solution. The presence (or
absence) of these functional groups allows for the identification of molecules present. Spectral
data below 1600 cm-1 is considered molecular fingerprint, and for the purposes of this lab, is not
analyzed. The two peaks at 1611.81 cm-1 and 1637.77 cm-1 represent carbon-carbon double bonds
that were expected in all of the isolated alkenes. No peak is observed in the 1750 cm-1 to 1735
cm-1 range, which shows that the acetate ion is not present, because no C=O is observed, so no
eugenol acetate in present as confirmed by the IR. The peaks at 2938.28 cm-1 and 2842.62 cm-1
represent the C-H bond in the alkanes found in all three molecules, and the peak at 3003.67 cm-1
represents the C-H bond in the alkenes found in all three molecules. These three peaks are not
diagnostic of any one molecule, but are expected. A peak was observed between 3580 cm-1 and
3650 cm-1 (representing an OH functional group), this peak was observed at 3511.36 cm-1. This
peak confirms the presence of eugenol because only eugenol contains an OH functional group.
The IR spectrum compares closely with a reference spectrum for Eugenol, further confirming
that the IR spectrum shows the presence of Eugenol.
In this lab, clove oil was isolated from ground cloves via steam distillation, which works
by allowing the clove oil to co-distill with water. Using a chemically active extraction, and rotary
evaporation, eugenol was isolated from this clove oil. Techniques in IR spectroscopy were used
to confirm the presence of eugenol, and Gas Chromatography showed that the extraction
methods were highly effective in isolating eugenol.

References:

Dalton, D.; Yip, M. Organic Chemistry in the Laboratory; D. Van Nostrand Company: New
York, 1979; pp. 26-30, 137-142

Eugenol - Infra Red Spectrum. http://www.chem.bham.ac.uk/schools/eugenolir.htm (accessed

Dec. 7, 2010).

Jones and Fleming. Organic Chemistry: 4th Edition. W.W. Norton & Company, Inc: New York,
2010; pp. 710-711

Figure 1: Structural Formulas Eugenol, Eugenol Acetate and Caryophyllene