Experiment Report of Organic Chemistry 3

I.

TITLE OF EXPERIMENT

Extraction, Separation and Purifying Technic Of Compound

II.

DATE OF EXPERIMENT

November 11th 2014

III.

END OF EXPERIMENT

November 11th 2014

IV.

PURPOSE OF EXPERIMENT :
-

To choose the suitable equipment each experiment that will be used

To choose the materials that needed on each experiment

To conduct isolation technique correctly

To choose suitable solvent for separation process

To conduct separation technique correctly

To conduct compound purification and recrystalization technique

To operate IR correctly

To identify compound based on fuctional group interpretation by using

IR spectrum

V.

BASIC THEORY

DEFINITION OF CHROMATOGRAPHY
Chromatography is a technique of separation of mixtures in various forms,
whether liquid, solid or gas. This method is used if the mixture can not be split
in any other way. Basic chromatography is the difference absorption of a
substance by substance mixtures lainnya.Jika mixture components (eg A, B and
C) with a solvent is passed through certain solids, then A, B and C will move at
different speeds, due to the absorption of the solids components are not the
same. Liquid or solvent that carries a moving part called the eluent or mobile
phase, while the solids are absorbing component called adsorpen or fixed
phase. Terms eluent harusdapat dissolve all komponendan can flow, the liquid

Experiment Report of Organic Chemistry 3

or gas.Eluen can be either pure substances or mixtures, eg pure pitch or alcohol
50%.
The most powerful components absorbed by the adsorbent will flow the
slowest (ie A) and conversely the lowest absorbed fastest flows (ie B), while
the absorption of C is between A and B. The longer the process flow the greater
the distance between the component and more perfect separation, but takes a
long tube as well as the eluent and adsorbent that much.
Components can be separated from other components by pushing out and
cut adsorbent based components. Each piece put into a solvent and filtered to
separate the adsorbent, and the solution will contain one component.
Components can be separated from the solvent by detilasi techniques or
recrystallization.
THE KINDS OF CHROMATOGRAPHY
Based on the type of eluent and adsorbent, chromatography can divided to
four ways, namely chromatography column, paper, thin plates, and gas.
Column Chromatography
Chromatography column chromatographic adsorbent is inserted into the
tube (pipe) glass. The adsorbent solids in powder form, for example alumina,
after separation of each component contained in certain areas chromatography
preformance tube.

Paper Chromatography
Paper chromatography is a type of chromatography that uses paper as an
adsorbent and liquid as eluen. Mechanical separation, the mixture of
components dropped on paper (used adlah paper chromatography) with a small

Experiment Report of Organic Chemistry 3

pipette, for example at two points p and q does not set the paper is hung so that
stable and in order eluan let rise slowly, carrying components terdapt at p danq
earlier. Eventually it will be seen apart from one another component, because
the difference in power absorbed in the paper.

Thin Layer Chromatography

Thin layer chromatography (TLC) using a thin plate (such as glass or
metal plates) were coated in solids as adsorbent and dried. After the slab drops
of the mixture to be separated and put into a vessel containing the eluent, such
as on paper kromatogrfi.

Gas Chromatography
Gas chromatography is gas chromatography using as eluennya, while the
components in the appliance will be converted into gas and flow with the
eluent. Flow velocity components will be different and lead to the separation of
the components with one another.

Experiment Report of Organic Chemistry 3

In a chromatographic technique, the sample is a mixture of different kinds

of components to be placed in the dynamic situation in the system consisting of
the stationary phase and the mobile phase. All the chromatographic separation
depends on the relative movement of each of the components between the two
phases. Compounds or components that restrained (inhibited) is weaker by the
stationary phase will move lebihcepat of the components are retained stronger.
The difference between the movement komponene with each other due to
differences in the adsorbent, partition, dissolution or evaporation between the
two phases. If these differences are big enough it will happen ppemisahan
perfectly. Therefore, in the selection of the mobile phase chromatography and
the stationary phase needs to be done in such a way that all components biased
to move with different speeds that can occur separation process.
Chromatography can be classified based on the type of phases used. In the
chromatographic mobile phase can be either gas or liquid and the stationary
phase can be either solid or liquid, then based on the moving-phase stationary
phase, there are four kinds of systems kromatogrfi, namely: gas-liquid
chromatography, gas chromatography-solid, liquid-solid chromatography and
liquid-liquid chromatography.
IR SPECTROSCOPY
Infrared spectroscopy (IR spectroscopy) is the spectroscopy that deals with
the infrared region of the electromagnetic spectrum, that is light with a
longer wavelength and lowerfrequency than visible light. It covers a range of

Experiment Report of Organic Chemistry 3

techniques, mostly based on absorption spectroscopy. As with all spectroscopic
techniques, it can be used to identify and studychemicals. For a given sample
which may be solid, liquid, or gaseous, the method or technique of infrared
spectroscopy uses an instrument called an infrared spectrometer (or
spectrophotometer) to produce an infrared spectrum. A basic IR spectrum is
essentially a graph of infrared light absorbance (or transmittance) on the
vertical axis vs. frequency or wavelength on the horizontal axis.
Typical units of

frequency

used

in

IR

spectra

are reciprocal

centimeters (sometimes called wave numbers), abbreviated as cm1. Units of IR

wavelength are commonly given in microns, abbreviated as m, which are
related to wave numbers in a reciprocal way. A common laboratory instrument
that uses this technique is a Fourier transform infrared (FTIR) spectrometer.
Two-dimensional IR is also possible as discussed below.
The infrared portion of the electromagnetic spectrum is usually divided
into three regions; the near-, mid- and far- infrared, named for their relation to
the visible spectrum.
The higher-energy near-IR, approximately 140004000 cm1 (0.82.5 m
wavelength) can excite overtone or harmonic vibrations. The mid-infrared,
approximately 4000400 cm1(2.525 m) may be used to study the
fundamental vibrations and associated rotational-vibrational structure. The farinfrared,

approximately

40010 cm1 (251000 m),

lying

adjacent

to

the microwave region, has low energy and may be used for rotational
spectroscopy. The names and classifications of these subregions are
conventions, and are only loosely based on the relative molecular or
electromagnetic properties.

Infrared spectroscopy exploits the fact that molecules absorb specific

frequencies that are characteristic of theirstructure. These absorptions

Experiment Report of Organic Chemistry 3

are resonant frequencies, i.e. the frequency of the absorbed radiation matches
the transition energy of the bond or group that vibrates. The energies are
determined by the shape of the molecularpotential energy surfaces, the masses
of the atoms, and the associated vibronic coupling.
In particular, in the BornOppenheimer and harmonic approximations, i.e.
when the molecular Hamiltoniancorresponding to the electronic ground
state can be approximated by a harmonic oscillator in the neighborhood of the
equilibrium molecular geometry, the resonant frequencies are associated with
the normal modes corresponding to the molecular electronic ground state
potential energy surface. The resonant frequencies are also related to the
strength of the bond and the mass of the atoms at either end of it. Thus, the
frequency of the vibrations are associated with a particular normal mode of
motion and a particular bond type.

(Figure: tools of IR spectroscopy)

The Absorbtion Infra Red

Experiment Report of Organic Chemistry 3

Fungsional Group

Absorbtion position

Intencity

Experiment Report of Organic Chemistry 3

CH
Alkane
CH3 , CH2
CH2
CH3
Alkene
C CH
Aromatic
Vinil
Distribution cis
Distribution trans
Alkyne
C CH
CC
OH ( hydroxyl group )
Monomer OH
Hydrogen bond OH
Double assosiasion OH
Carboxylic acid OH
NH (Amine and amide
group )

2980 -2850 ( cm-1)

1485 - 1430
1380 - 1365

m
m
s

3100 - 3030
3030
995-985 , 915-905
690
970 960
895 - 885
3300
2140-2100

m
w
s
s
s
s
m

3650 3590
3550 3450
3400 3200
2700 2500

s, tajam
s
s, lebar
w

Amine primer
Amine sekunder
Amide primer

3500, 3400
3500-3300
3500,3400

m
m
m

Hydrogen bond
Amide sekunder
Hydrogen bond
Ester

3350-3180
3460-3400
3320-3140

m
m
m

H CO O R
CH3CO O R
Fenil ecetic

1200-1180
1250-1230
1205

s
s
s

1200-1150
1310-1250, 1150-1100

s
s

1400-1100
800-600
600-500
500

s
s
s
s

RCO O R
aromatic
CX
CF
CCl
CBr
CI
Carboxylic acid
anhydrous

Experiment Report of Organic Chemistry 3

Saturated bond
A ring have five saturated
memebers
Ketones
Saturated bond
Aldehide
Saturated aliphatis

1850-1800
1790-1740
1870-1820

s
s
s

1800-1250
1725-1705

1740-1720

Experiment Report of Organic Chemistry 3

VI.

TOOLS AND MATERIALS

Tools:
-

Capillary

(1 item)

Filter paper

(1 item)

5 ml vial

(1 item)

Pipette

(10 items)

10 cm x 20 cm x 20 cm chamber (1 item)

Spatula

(1 item)

10 ml graduated cylinder

(1 item)

100 ml beaker glass

(1 item)

Stir bar

(1 item)

UV lamp

(1 item)

Set of instruments IR

(1 item)

Pencil 2B

(1 item)

Tweezers

(1 item)

Small glass funnel

(1 item)

Materials:
-

Sample

Distillate of methanol

Distillate of hexane

Experiment Report of Organic Chemistry 3

-

Chloroform

4 cm x 20 cm TLC plate

Fecl3 reagent.

Experiment Report of Organic Chemistry 3

VII. PROCEDURE

1.

Preparation of equipments
-Clean the practical desk and equipments for experiment
Ready equipments

2. Chromatography Test

15 mg Sample
A

TLC plate 4 x
20 cm

-Diluted with

-Given line upper

1mL methanol

0,5cm and lower

1,0cm
-Given dots on lower
line that has distance
0,5cm

-Spotted sample A on the dots in

TLC plate until it runs out

Spotted TLC Plate

Experiment Report of Organic Chemistry 3

Spotted TLC Plate

-Put into chamber that filled with
20mL eluent
-Let the elusion process until
almost reached the upper line
TLC Plate
-Taken TLC plate carefully, let it dry
-Taken the spot bond
-Put into filter paper that has been set
-Soaked with 1mL methanol
-Filtrated

Residue

Filtrate
-Evaporated
-Recrystalized
Powder of sample
-Identified by using IR

Print out

Experiment Report of Organic Chemistry 3

IX.
X.

ANALYSIS DATA
CONCLUSION

Experiment Report of Organic Chemistry 3

REFERENCES

Anwar, Chairil, dkk. 1994. Pengantar Praktikum Kimia Organik. Yogyakarta :

FMIPA Universitas Gadjah Mada
Carey, Francis A. 2006. Organic Chemistry Sixth Edition. New York: Mcgrawhill.
Fessenden RJ. Fessenden JS. 1991. Kimia Organic, Edisi ketiga terjemahan A.
Harayana Dudjaatrata, Jilid 1 dan 2. Jakarta: Penerbit Erlangga.
Said, Moh, dkk. 1985. Penentuan Struktur Molekul. Surabaya : Jurusan Kimia
IKIP Surabaya

Tim Dosen Kimia Organik. 2013. Penuntun Praktikum Kimia Organik II.
Surabaya : Unesa Press.
Ventii. 2013. Laporan Ekstraksi. (online)
http://www.scribd.com/doc/129514725/LAPORAN-EKSTRAKSI
(Accessed on November, 25 2014)

Experiment Report of Organic Chemistry 3

ANSWER QUESTION
1. What is the technique of extraction, separation and purification of a
compound?
Answer:
Mechanical extraction, separation and purification of a compound, the
three techniques all have the same principle of the separation of the
substance of the mixture into components with each method
2. What is a chromatographic technique? why is selected in the
preparative TLC separation above?
Answer:
Chromatography is used to separate the substance of the mixture into its
components. All forms of chromatography work based on this principle.
Chromatography is a separation technique based on the difference in
propagation speed mixture components in a particular medium. In
chromatography, the components to be separated between two phases,
namely the stationary phase and the mobile phase. Stationary phase while
the mixture components will withstand the mobile phase will dissolve the
mixture components. Components are easily retained on the stationary
phase will be missed. While the components are soluble in the mobile
phase will move faster. Used preparative TLC in order to obtain a stable
quality of the separation of organic compounds in the sample. It is
appropriate that the TLC-P used absorbent (stationary phase) with a
thickness of 0.5 to 2 mm of silica gel or aluminum oxide and a large plate
(size 20x20 cm and 20x40 cm).
3. What is the eluent and what type of solvent used as the eluent at the
top?
Answer:
The eluent is a mobile phase plays an important role in the process of
elution for the feed solution (feed) to pass through the stationary phase
(adsorbent). The type of solvent used as eluent is hexane, chloroform,
methanol.
4. Why do purification techniques, explain the basic principles of
recrystallization?
Answer:

Experiment Report of Organic Chemistry 3

Purification is done to separate the pure substance with dirt or pollution
substances.
Recrystallization basic principle: the crystallization process begins by
adding the compound to be purified with hot solvent until the solubility of
the compound at the level of super-saturated. In these circumstances, if the
solution is cooled, the molecules of dissolved compounds will be sticking
together, grows into crystals that will settle at the bottom of the container.
While the dirt does not come precipitate dissolved.
Formation of the crystal itself consists of two phases. The first stage is the
primary nucleation or formation of the core, which is the stage where the
crystals begin to grow but do not settle. This stage requires a
supersaturated state of the solute. When the solution was cooled, the
solvent can not "hold" all za-solute, resulting molecules are separated from
the solvent sticking together, and began to grow into a crystal nucleus. The
more cores are joined, it will be the sooner the crystal growth.
The second stage after the primary nucleation is secondary nucleation. At
this stage petumbuhan faster crystal, which is characterized by mutual
attachment of the cores into solid crystals.
5. What are the functions and benefits of the tool / instrument IR
spectrometer?
Answer:
Equipment / IR spectrophotometer instrument is a device used to record
the infrared spectrum trading and easy to use routinely. Infrared
spectrophotometry is very important in modern chemistry, who major in
organic fields. Were instrumental in the discovery of functional groups, the
introduction of the compound mixture analysis.
6. The results of the data analysis and your identification, compound
what can you charge?
Answer :
(VITA INI
AKU

GA

BISA

NGERJAKAN

KARENA

BERHUBUNGAN SAMA PUNYAMU HASIL ANALISIS MU)

Experiment Report of Organic Chemistry 3

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