Steam Distillation of Cloves

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Steam distillation of cloves produced 0.53g of an oil which contained in its IR spectrum the functional groups O-H (at 3520 cm-1), sp2 C-H (3080 – 3000 cm-1), aliphatic C-H (2980 – 2940 cm-1), and both alkene C=C (at 1640 cm-1) and aromatic C=C (at 1514 cm-1). The IR spectrum is attached to this report. These data are consistent with the structure of eugenol, shown in Figure 2 below:

In addition, the IR of the product from the steam distillation of cloves closely corresponds with that of an authentic sample of eugenol shown in the lab text.9 Therefore, it can be concluded that the oil which was isolated from cloves is in fact, eugenol.

0.53 g of eugenol was recovered from 5 g of cloves. This corresponds to a percent recovery of 7.46%:
Amt. Eugenol isolated0.53 g
% Recovery = ------------------------------ = -------------- x 100 = 10.6%
Amt. Cloves used5 g

In this experiment, it was shown that about 10.6% of an oil could be recovered from cloves by steam distillation. This oil was identified as eugenol by comparison of its infrared spectrum with an authentic sample.

2.) The active component is Eugenol. It is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is slightly soluble in water and soluble in organic solvents. Clove oil is soluble in dichloromethane so its easily extracted by evaporating dichloromethane. Eugenol has a high boiling point (254 oC), and many organic compounds decompose at such high temperatures. Steam distillation allows eugenol to be distilled at a much lower boiling point (< 100 oC), thus minimizing the potential for decomposition.
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