Abstract:

The purpose of this experiment was to use techniques to do some isolation of

natural products like solid cloves. These techniques will include task that involve
steam distillation, drying organic solutions, liquid/liquid extraction and infrared
spectroscopy. We had 1.01g amount of crushed clove and found out it had a boiling
point of 254
o
c. It was shown that about 9.83% of an oil was be recovered from cloves by steam
distillation. This oil was identified as eugenol by comparison of its infrared spectrum
with a sample. Steam distillation of cloves produced 0.0983 g of an oil, which
contained in its IR spectrum the functional groups O-H (at 3599.15 cm-1), sp2 C-H
(3054.26 cm-1), sp3 C-H (2905.56 cm-1), and both alkene C=C (at 1613.26-1637.90
cm-1) and aromatic C=C (at 1432.79-1513.81 cm-1) and mixed unsaturated C-OC(at 1207.00-1265.41 cm-1). The IR spectrum is attached to this report. 0.0983 g of
eugenol was recovered from 1.01 g of cloves. This corresponds to a percent
recovery of 9.83%.
Introduction:
The point of this was to learn the techniques of isolation of natural products. Those
techniques will include task like the importance of steam distillation, drying organic
solutions, liquid/liquid extraction and infrared spectroscopy. We will be isolating the
volatile flavor and odor in crushed cloves by running a steam distillation. We will be
separating eugenol from the water traveling through liquid/liquid extraction. By
separating the eugenol from the water, it will produce a pentane that will disperse
utilizing a solid drying agent. Steam distillation: The point of this was to use an
azeotrope to isolate the organic compound from a solid. When you distill water from
an azeotrope will form water at a boiling point of 100
o
c, and eugenol at a boiling point of 255
o
c. We will be boiling the mixture at a high boiling point at a low temperature by
using water and bromobenzene, both liquids are immiscible. Liquid extraction:
Liquid extraction is the ability of insoluble liquids to extract one solute from one
liquid into a different liquid. The two different layers can be removed by draining the
bottom layer through a funnel. Being able to separate the two layers is important
because different solutes can go into different layers. Drying We will be tracing the
amount of water that is dissolved into an organic solvent, by tracing the amount of
water removed by the aid of a drying reagent. A drying reagent is added to the
solution and swirled for a few minutes until the solid reagent has removed the
water. Infrared Spectroscopy (IR) Infrared uses infrared region of the
electromagnetic spectra, when an atom is excited with radiation bending will occur.
Experimental:

The experimental procedure for this lab was found in the PSU Lab manual, and all
of the chemicals used in this experiment were obtained from the PSU chemistry
stockroom. Add 1.0 g of freshly crushed, 10 mL of H2O and a magnetic stir vane to
your 25 mL round-bottom. Take a Claisen head fitted with a compression cap, then
attached to the round bottom flask with the threaded adaptor. Use a three prong
clamp, attached to a ring stand, clasp your apparatus to flask and leave it resting in
a sand bath on top of a hotplate. A Hickman with a compression cap and a water
condenser attached to the claisen head. Loosely clasp the water condenser to the
ring stand with a clamp. Connect the water tubing to the water condenser, gently
turn on the water. Have the TA check you set-up before you start. Turn the hot plate
on and warm the sand bath to approximately 160-180 oC. Maintain approx. 10 mL of
water in the round-bottom flask. We will need to collect approx. 5-6 mL of distillate
in your tube. Pre-mark your centrifuge tube to 5 mL with a Sharpie.

Turn the heat and the cooling water off after collecting 5-6ml. Add approx1.5 g of
solid NaCl and 3 ml of pentane to the tube, cap the tube and thoroughly shake. Drip
the pentane/ eugenol mixture through a 5 cm plug of anhydrous Na2SO4 collecting
the eluent in a pre-weighed 25 mL beaker re-extract the aqueous layer two
additional times with 3-4 mL of pentane. Rinse the Na2SO4 plug with 3-4 mL of
pentane. Swirl the beaker on a warm hot plate to remove the pentane. Once the
pentane has been removed, weigh the cooled beaker. Find the weight of eugenol
and calculate the percent recovery from the original weight of cloves. Record the
infrared spectrum of eugenol as a liquid on sodium chloride plates. NEW: After
collecting the 5-6 mL of distillate in the tube, turn the heat and the cooling water
off. Add approximately 1.5 g of solid NaCl and 3 ml of pentane to the tube, cap the
tube and shaking. Allow the mixtures to separate and remove the pentane layer w/
piper. Transfer the pentane/ eugenol mixture to a beaker.

Re-extract the
aqueous layer two additional times with3
-4 mL of pentane. Transfer the pentane/ eugenol mixture to the same beaker. Add
anhydrous Na
2
SO
4

until the solution becomes clear. Gently pour the solution to another

mL beaker. Swirl the beaker on a warm hot plate to remove the pentane. If the plate
is hot the mixture could bump or catch on fire.
Clean-up and Waste Disposal
The residue in the round-bottom flask from the steam distillation can be put down
the drain. Clean the flask with soap and water, with a final acetone rinse. Clean the
remaining parts with acetone and dry all glassware. Put extra acetone in acetone
waste
Results:
Initial material: 1.01grams of crushed cloves %recovery= .0983 grams of oil/
1.01grams of crushed cloves X 100%= 9.83% recovered On the back of the
lab/attached on IR spectrum graph
Discussion:
Some sources of error that could of happen was not having grounded the cloves
well enough, may not have distilled the cloves long enough in high of enough heat,
and may have had loose connectors between my glassware that would account for
a lower percent yield. Also the distillation rate may have been too fast which could
lead to the collection of a less pure distillate, and subsequently a higher percent
recovery than the actual value.
Conclusion:
The purpose of this was to learn the techniques of isolation of natural products.
Those techniques will include task like the importance of steam distillation, drying
organic solutions, liquid/liquid extraction and infrared spectroscopy. In this
experiment, it was shown that about 9.83% of an oil could be recovered from cloves
by steam distillation. This oil was identified as eugenol by comparison of its infrared
spectrum with a sample. Steam distillation of cloves produced 0.0983 g of an oil,
which contained in its IR spectrum the functional groups O-H (at 3599.15 cm-1), sp2
C-H (3054.26 cm-1), sp3 C-H (2905.56 cm-1), and both alkene C=C (at 1613.261637.90 cm-1) and aromatic C=C (at 1432.79-1513.81 cm-1) and mixed
unsaturated c-o-c(at 1207.00-1265.41 cm-1). The IR spectrum is attached to this
report. 0.0983 g of eugenol was recovered from 1.01 g of cloves. This corresponds
to a percent recovery of 9.83%.
Reference:
Organic Chemistry Laboratory I, CH 337M; Department of Chemistry, Portland State
University: Portland OR; p 45.
Questions:
1.

Suppose a reaction mixture containing 30 g of malononitrile, CH2 (CN) 2 is dissolved

in 300 mL of water. The malononitrile is to be isolated by extraction with ether. The
solubility of malononitrile in ether at room temperature is 20.0 g per 100 mL and
that in water is 13.3 g per 100 mL. What weight of malononitrile would be recovered
by extraction with (a) three 100-mL portions of ether; (b) one 300-mL portion of
ether?
a. 20g/13.3g=15.5=k x/100/30-x/300=1.5 x=10 x/100/20-x/300=1.5 x=6.67
x/100/13.33-x/300=1.5 x=4.43 4.43+6.67+10=21.11g b. x/30-x=1.5 x=18g

2.

Explain what is meant by "venting" an extraction. Why is it important to do this?

Venting was when we had to open the cap of the tube, so we can let gas go out. It
was important to do this, because this allowed gas to go out so that it can release
pressure. If we got the pressure high, it could cause it to explode
. 3.

Several students in the lab neglected to put the cap back on the bottle of anhydrous
Na2SO4 after they weighed some out for use in the eugenol isolation. Explain why
this isn't a good idea.
Na2SO4 is a dry agent it is used to remove the water from the compound. If you
leave it open, it can
react with water in the air. If this happens then it won
t be as good as drying.
4.

a. Deduce a structural isomer of C4H9NO that would fit the following IR. b. Tell me
what types of bonds are represented at 3366 and 3200 cm-1, 2950 cm-1, and 1690
cm-1. You will need to use appendix D. Note the numbers in the structure may be
slightly different that in appendix D.
Stretching 3366 & 3200 cm
-1
= primary N-H bond Stretching 2950 cm
-1n
= the sp3 C-H bond Stretching 1690 cm

-1
= carbonyl (C=O) bond