Major Component from Clove Oil, Identified by IR Spectra and Molecular Formula

Scott Klasen, Wesley Applequist

12/8/2010

Experiment 10

Purpose:

In this experiment, the essential oil found in clove buds was extracted. What’s more is the

structure of the major component in the oil was to be determined. The compound is known to

have a molecular formula of C10H12O2, an infrared spectrogram of the major component was

interpreted to determine the functional groups present in the molecule.

Procedure:

To begin, a distillation apparatus was assembled. The apparatus is pictured below:

Thermometer

H2O

Essential oil

Clove mixture
 Image 1: Modified distillation apparatus

This is similar to a normal distillation apparatus, a noteworthy difference is the addition

of a separatory funnel. In this funnel, water was held and added to the distillation mixture, as the

water boiled off before all the oil was extracted.

4.920 grams of ground cloves were added to a boiling flask along with 50 mL H2O. Cold

water was run through the condenser and the boiling flask was connected to the distillation

apparatus. Heat was applied to the flask (denoted by ∆). The distillation continued for about 90

minutes, in which time an additional 300 mL of water was added to boiling pot. When the

distillation was stopped there were 95 mL of distillate.

After distillation, the oil needed to be separated from the water mixture. To do so, the oil

was extracted with two 40 mL portions of dichloromethane. The dichloromethane solution was

dried with magnesium anhydride and then evaporated over hot water into a cold water trap. In

all, (Some amount) grams remained. This is believed to be the essential oil found in cloves.

IR spectrogram data was provided by the lab instructor; its interpretation and presentation

follows.

Results:

As stated, the ground cloves were distilled in a modified distillation apparatus. The

temperature of the vapor was 100°C, so water was added to the system as it was distilled into the

oil. After 95 mL of distillate were collected, it was washed with dichloromethane and dried with

anhydrous magnesium sulfate.

Reagent Quantity Used

Ground Cloves 4.92 g
H 2O 300 mL
CH2Cl2 80 mL
MgSO4 ~0.10 g
 Quantity
Yielded
Essential Oil 95 mL
Major Component
Table 1: Reagents, Products, and Quantities

An IR spectrogram was provided for both the minor component and major component in

clove oil. Areas of note in the minor component are: a very active band over 3000 1/cm, there are

also large bands over 1800, 1500, and 1200 (1/cm). For the major component: a comparatively

less active band over 3000 1/cm, a sharp band above 3500 1/cm, and some sharp bands between

1600 and 1300 (1/cm) are of note.

Image 2: IR Spectra of Major Component and Minor Component

Discussion:

The purpose of this experiment is to identify the molecular structure of the clove oil

extracted from the raw cloves tested. The chemical structure of the clove oil component in this

experiment is C10H12O2. There are multiple structures that can be formed by this chemical

formula, but based on the results acquired from this experiment certain functional groups can be

identified to help figure out the structure of the major component in this experiment.

The IR spectrogram results of the major component show that there are three sharp bands

(image 2). The single sharp band above 3500 1/cm possibly suggests that there is a methyl group

attached to oxygen separate from the rest of the structure. This observation is supported by a

short wide active band over 3000 1/cm that appears to have a total of eight spikes and is about a

third of the height of the sharp band above 3500 1/cm. This suggests a ring structure due to the

number of hydrogen atoms in the structure and this is supported by the location of short wide

active band being around a wavelength of 3000 1/cm. The lack of a second spike like the one

above 3500 1/cm suggests that the second oxygen contributes to an alcohol group. The two sharp

bands in the IR spectrogram between 1300 and 1600 1/cm may possibly point to an alkene.

Taking this information into consideration the major product of clove oil appears to have a

structure like the one shown below:

References: