Experiment 9: Isolate of Citral from Lemongrass Oil

Purpose
To isolate citral from Lemongrass Oil by steam distillation, and analyze using infrared
spectroscopy.
Theory
Citral has two isomers, which are geranial (the trans isomer), and neral (cis isomer),differ
only in the spatial orientation about the double bond that contains the aldehyde functional group.
Citra is relatively volatile and water insoluble, which makes it suitable for isolation by
steam distillation. As long as the two liquids are immiscible, the boiling point of the mixture
remains constant, and the distillate composition remains constants. The boiling point of the
mixture will be less than the boiling point of the lowest boiling point component. The condensate
composition from steam distillation depends on the molar masses of each component and upon
each of their vapor pressures at the boiling point of the mixture.
Reaction

Percent recovery
o Mass of 1.5mL lemongrass 1.5

ml0.893 g
=1.3395 g .
1 ml

o Weight of citral 1.09 g .

1.09
%recovery=
100=81.37 .
o
1.3395
Percent Composition.
From GC results, percentage of citra = %area = 80.19%.
Methods/Procedures

The experiment was followed verbatim from the textbook as found on page 75, 76, 77,
and 78.
Important: Citral can be irritating to the nose and eyes in its concentrated form. Do not
breathe its fumes heavily or get in eyes. BE sure the steam distillate is cooled below 300C before
extraction of citral with diethyl ether; otherwise, excessive pressure may develop in the
separatory funnel and blow out the stopper. Diethyl ether is extremely flammable. Be certain
there are no hot objects nearby during its use or its removal from the citral.
Observations/Results
Lemongrass oil was yellow liquid, and insoluble in water. It has a strong lemon odor.
Liquid after steam distillation was white, and had lemon odor. The percentage of recovery was
81.37%. Base on GC result, percentage of citral in liquid was 80.19%. From the IR result, we
can see 2 peaks, first peak (3040-2880) shows (sp2) C-H (3040-3000) which means an alkene
group, and (sp3) C-H (3000-2880). The second peak (1700) represent a C=O Aldehyde groups.
Discussion/Conclusion
We isolated citral from Lemongrass Oil by steam distillation, and analyzed the liquid
using infrared spectroscopy and gas chromatography. The results showed that we go 81.37%
recovery, which was high, and the liquid contains 80.19% citral. From IR result, we can
recognize alkene groups and C=O aldehyde groups, which are functional groups of Citral.
Exercises
1. a) 1,2- diaminocyclehexane has two stereocenters, so it has 22 = 4 stereoisomers.
b) We can see that cis stereoisomer has a superimposable mirror image, and form a meso
compound, so it dosent have an enantiomer. Therefore 1,2- diaminocyclehexane has only
three stereoisomers.
2.

3. a) They are diastereomers, so they have different physical properties.

b) They are enantiomer, so they have the same physical properties.