VIETNAM NATIONAL UNIVERSITY – HCMC

INTERNATIONAL UNIVERSITY

REPORT
Subject: Organic chemistry laboratory.
Lab partner: Lê Hồ Thi
Đỗ Trương Anh Thư
Bùi Hữu Đức
Trần Hoàng Thanh Tuyền
Instructor’s name : Dr. Hoang Le Son

Semester II
2016-2017
Organic chemistry laboratory 1

CONTENT
Experiment 1 : Melting point determination……………..…2
Experiment 2 :
Recrystalazation………………………..........7
Experiment 3 : Thin layer chromatography…………........13
Experiment 4 : Colum chromatography……………………
20
Experiment 5 : Sample distillation …………………………
24
Experiment 6 : Reflux
distillation…………………………...28
Experiment 7 : Liquid liquid extraction……………………32
Experiment 8 : Fischer ester
synthesis……………………..37
Experiment 9 : Solvent effects in an sn1 solvolysis reaction
a kinetics study…………………………………………….
…..41
Organic chemistry laboratory 2

EXPERIMENT 1 : MELTING POINT DETERMINATION

I. ABSTRACT
Melting point can be used to identify a substance and as an indication of its purity.
The purpose of this experiment was to understand how to determine the melting points of
pure substances and compounds mixture; how to use melting points to identify unknown
substance. A melting point apparatus was used to measure the melting point of two pure
substances, Pure Urea and Pure Cinnamic Acid, and the melting points of mixtures that
consisted fixed ratios of the two pure substances. A hypothesis for this experiment is that
all the mixed samples of the solids will attain a melting point lower to that of the samples
of the pure solids because if a pure solid has impurities, which are the mixtures, then the
melting point of the pure substance in a mixture will have its melting point depressed by
a few degrees from that of the original melting points of the two pure substances. The
data collected is compared to the melting point theory to prove if the melting ranges of
the pure substances and the mixtures stayed consistent with the theory.
II. INTRODUCTION
The melting point of a compound is determined by the intermolecular forces between
each of the molecules in the compound such as hydrogen bonding, dipole-dipole or van
der Waals interactions. Melting point is also looked at as the melting range meaning the
time start of which the compound starts to liquefy to when the solid is completely melted.
Larger molecules will have higher molecular forces and will take a lot of heat to break
the molecules down to a liquid.
Melting point is the value to evaluate the purity, identity and characteristics of a
substance. Many, potentially conflicting, factors play a role in determining melting points
including molecular shape, interactions between groups within the molecule, and the
degrees of freedom the molecule possesses within the crystal. The melting point of a
solid can be easily and accurately determined with only small amounts of material and, in
combination with other measurements, can provide rapid confirmation of identity. The
most accurate method of determination is to record a cooling curve of temperature versus
time. However, this approach requires quite large amounts of material and has been
exclusively replaced by the capillary method. This method uses a narrow capillary tube
and a Melting Point apparatus. The rate of heating this tube is controlled and kept
relatively low.
Organic chemistry laboratory 3

III. MATERIAL AND METHOD

Prepare the compound mixture of pure cinnamic acid and pure urea : Mixed cinnamic
acid and urea in molar percentage ratios of 100: 0, 90:10, 80:20, 70:30, 60:40, 50:50,
40:60, 30:70, 20:80, 10:90 and 0:100, which is 0.5g of total.
Input each of the pure and mixed solids into individual capillary tubes by carefully
scooping the solids into the tubes. Amount of solid in the capillary tubes should
approximate to about 4 mm in height. Invert the tubes so that the open end faces up and
tap the bottom of the tube to get the solids to the bottom of the tube. A long hollow glass
tube may be used with this process by dropping the capillary tube into the glass tube to
enable the capillary tube to bounce within the perimeters of the glass tube so that the
solids are agitated to migrate to the bottom of the capillary tubes.
Place the capillary tubes into the melting apparatus. Adjust the rate of heating so that the
apparatus heats up the tubes at a moderate rate. When the temperature reaches 15-20
degrees Celsius
below the Pure Cinnamic Acid: Pure
Melting Point (Celsius) expected
urea
melting point, then
adjustments 0:100 133.3 could be
made so that 100:0 131.6 the
temperature rises 1-2
degrees per 90:10 126.1 minute.
Record the melting
80:20 111.2
range. The melting
range is 70:30 105.4 determined
at the time when the
solid starts to 60:40 102.8 melt to the
point in 50:50 98.9 which only
liquid occupies the
capillary tube 40:60 97.9
IV. 30:70 98.4

20:80 115.9

10:90 127.0
RESULTS
Table 1 : The melting point of pure cinnamic acid, pure urea and mixed
cinnamic acid and urea in molar percentage ratios
Organic chemistry laboratory 4
Organic chemistry laboratory 5

Figure1: Graph of the melting point as the composition of a mixture of

cinnamic acid and urea is changed from pure cinnamic acid to pure urea. 

Image1: The melting point of unknown substance.

V. DISCUSSION
Sample for melting point determination should be:
+. Finely ground particles of the compound are necessary for efficient and uniform
packing in the sample capillary tube. This allows good heat transfer. If the particles are
too coarse, they will not pack well, causing air pockets that slow heat transfer and heat is
not distributed evenly.
+ It is important that sample is completely dry. Incomplete drying of a sample may result
in the presence of impurities which leads the melting point is both lowered and
broadened. For example, if the normal melting point of a substance is 201oC – 210oC, an
improperly dried substance may contain impurities thus lowering and broadening the
melting point range to something like 150oC – 160oC.
+ That do melting point determination on small sample is better than on large sample. It
would take hours and hours to heat the entire sample up so slowly from outside to the
inside to reach the same temperature everywhere, because for a sharp melting point
determination the temperature differences (outside-inside) should be as small as possible.
+ It is imperative that the heating rate be carefully controlled once near the suspected
melting point of a sample. If heating in a temperature that much lower than its melting
Organic chemistry laboratory 6

point, it will take lots of time for the sample to reach it. Then, the temperature is increase
slowly to the melting point in order to get an accurate measurement.
The table 1 illustrates the data collected during the melting point experiment. For the
pure substances pure Urea and Pure Cinnamic acid, the melting point of cinnamic acid
was recorded at 131.6ºC and Urea at 133.3ºC. The melting point range for the pure
cinnamic acid is 131-133°C, so that cinnamic acid solid was quite pure compound.
Besides, the melting point of urea was higher than the melting point range for pure urea
130-132°C, so that urea powder was not pure compound.
However the mixtures used to conduct the experiment will have a different result
from that of pure substances. The melting ranges of the mixtures also stayed consistent
with the melting point theory which generally states that impure substances will have a
large melting range because impurities within the pure substances will depress the
melting point by a few degrees from that of the melting point when the substance is pure.
The graph shows that the mixing of the two substances resulted in a much lower melting
point. The mixing of urea combined with cinnamic acid also resulted in a lower melting
point than that of pure urea. These results show that impure substances have lower
melting points and wider ranges of melting point temperature than pure substances. It
would not be possible to employ that graph to determine the composition of an unknown
cinnamic acid/urea sample. For instance, if the melting point is recorded at 120ºC and
base on that graph, it will have 2 choices: 24% cinnamic acid and 76% urea or 82%
cinnamic acid and 18% urea. It is hard to determine which one is correct.
Potential errors in this experiment might’ve happened when the solids have to be
carefully crushed when making the mixtures. Improper crushing of the solids and
mixtures could result in insufficient mixtures and create confusion with the melting
points of the mixtures. In the future if ever the experiment is attempted again, more
attention will be implemented in mixing the mixtures to enable accurate melting points
during the experiment.
VI. CONCLUSION
Melting point determination is to use the melting point range of a substance to help
determine its general purity. The smaller the melting point range, the more pure the
substance is. The larger the melting point range, the less pure the substance is.
VII. REFERENCES
“Experiment 1: MELTING POINT DETERMINATION” Organic Chemistry Lab
Manual. International University HCMC-VNU, 2016 
"Why is it necessary to use a powder rather than a crystalline sample when
determining melting point." Answers. Answers Corporation, n.d. Web. 
DeQuint, Joppe. "Why is it not a good to do melting point determination on large
samples?" Answers. Answers Corporation, n.d. Web. 
Http://independent.academia.edu/jacksonvin. "Chem lab report 1-1." Academia.edu -
Share research. N.p., n.d. 
Organic chemistry laboratory 7

EXPERIMENT 2: RECRYSTALIZATION
I. ABSTRACT
“Recrystallization is a process whereby a crystalline material dissolves in a
hot solvent, then returns to a solid again by crystallizing in the cooled
solvent” [1]. Recrystallization was attempted in this experiment to purify the
organic compound, Benzoic Acid. The purpose of this experiment was to
recover benzoic acid from a sample of an impure organic compound and the
good solvent is also determined among water, methanol and ethanol. This
was done by using recrystallization techniques. The recrystallized benzoic
acid, with a mass of 0.17g was recovered from a 0.5g sample of impure
benzoic acid. Percent recovery of Benzoic acid was found to be 34%. The
result also shows that methanol is a good solvent for recrystallization of
benzoic acid. One more purpose of this lab experiment is to recrystallize an
unknown compound and determine the identity via melting point
determination.
II. INTRODUCTION
Recrystallization is the process when solute dissolves in a hot solvent and
then returns to a solid again by crystallizing in a cooled solvent (mohrig
2010). Pure compounds contain strong molecular bonds which allow them to
Organic chemistry laboratory 8

form a crystalline lattice whereas impure substances boast weaker bonds

which don’t allow them to form a crystal lattice. This allows the impure
substances to separate itself from the crystallized benzoic acid. The
crystalline substance is dissolved in a hot solvent which will increase the
solubility of the solution and eliminate any impure substances. Then the
solution is cooled in an ice-water bath which decreases the solubility of the
solution causing the pure substance to recrystallize. Slow cooling of the
substance promotes formation of purer crystals, because the molecules of the
impurities do not fit well with the newly forming crystals (mohrig 2010).
Recrystallization is the primary method for purifying solid organic
compounds. These impurities may include a combination of insoluble,
soluble, and maybe colored impurities. Recrystallization depends on the
solubility of difference substances in a given solvent [1]. In general,
recrystalization is carried out following these steps: choosing the best
solvent for recrystallization, dissolving the sample by this solvent in hot
water bath, filtering this hot solution, cooling the filtered solution, filtering
this cold solution, washing and drying the crystals. 
III. MATERIAL AND METHOD
Material: benzoic acid, distilled water, methanol, ethanol, unknown sample 
Equipment: weigh bottles, vials, filter paper, Erlenmeyer flask, stirring rod,
water bath, funnel, pipette, pump, Büchner funnel, graduated cylinder.
A portion of Benzoic Acid, provided by the TA. About 0.5 mg of
Benzoic acid was used. In another beaker, about half of the beaker was filled
with the solvent (water) and brought to a boil using a hot plate. At the same
time, we test the good solvent amomg water, methanol, ethanol by disolving
0.5g sample in three vial with three solvent above and observe the solution
of each sample in each vial at the room temperature. Then we choose the
good solvent by yourself and take this for recrystalization. Once the solvent
was boiling, about 2 mL of the boiling solvent was transferred to the flask
containing the Benzoic acid using a Pasteur pipet. The flask containing the
solution was heated again to increase the solubility of the Benzoic acid.
Once all of the solute completely dissolved inside the solvent, there was
solid material floating at the top of the solution which indicates that there
was impurities present with the Benzoic acid. A pipet was used to decant the
solution into another flask leaving the impurities behind. After the transfer
of the solution, the solution was left to cool on the bench to induce crystal
formation. It was left on the bench for about 10 minutes. The formation of
white crystals indicates the crystallization of the Benzoic acid. Once the
crystals began to form, the flask with the crystals was placed into an ice bath
to complete the recrystallization process. The flask was left in the ice bath
Organic chemistry laboratory 9

for about 10-15 minutes. After being in the ice bath, the flask now contained
a slurry of the Benzoic acid crystals. After the cooling of the Benzoic acid
crystals, the product was taken then taken to an apparatus to be vacuumed
filtered. Vacuum filtration is used to completely separate a solid from the
liquid with which it is mixed. The apparatus was set up by attaching a water
aspirator to a faucet. Then thick rubber tubing was used to connect the water
aspirator to a filter flask with a Buchner funnel resting on top of the flask. A
stand was used to suspend the filter flask for easier operation. When
filtering, the water aspirator was turned on first to verify a suction coming
from the tube before connecting it to the filter flask. Once vacuum is
considered satisfactory, the tube was then connected to the filter flask. Filter
paper was placed on top of the opening of the Buchner funnel to prevent the
crystals from being sucked into the filter flask. Once the apparatus is
complete, then the slurry of Benzoic Acid crystals was dispensed into the
Buchner funnel to filter out the crystals and excess solvent. After the crystals
have been filtered, the crystals was transferred to a vial, to allow the crystals
to dry before weighing. The weight of the vial was taken before hand.
Finally, weighed, recorded the result, calculated the percent recovered using
the following written formula
weight of benzoic acid after recrystalization
% Recovered = weight of benzoic acid before recrystalization x 100

Besides, we determine the unknown sample by using Mel-Temp

apparatus to determine the melting point of it. About 4mm of the unknown
sample was transferred to a capplillary tube. Then the cappilary tube was
transferred to a Mel- Temp apparatus and record the result.
IV. RESULTS
Organic chemistry laboratory 10

Figure 1 : Crysral of Benzoic acid after recrystalization

Figure 2 : Melting point of unknown sample

V. DISCUSSION
The first consideration in purifying a solid by recrystallization is to find a
suitable solvent. The ideal properties should be possessed by a
recrystallization solvent: 
+ The compound should be very soluble at the boiling point of the solvent
and insoluble in the solvent at cold temperature. This difference in solubility
at hot versus cold temperatures is essential for the recrystallization process.
If the compound is insoluble in the chosen solvent at high temperatures, then
it will not dissolve. If the compound is very soluble in the solvent at room
Organic chemistry laboratory 11

temperature, then getting the compound to crystallize in pure form from

solution is difficult. 
+ The unwanted impurities should be either very soluble in the solvent at
cold temperature or insoluble in the hot solvent. In this way, after the impure
solid is dissolved in the hot solvent, any undissolved impurities can be
removed by hot filtration. After the solution cools and the desired compound
crystallizes out, any remaining soluble impurities will remain dissolved in
the solvent. That’s why crystals are washed with additional solvent when
collected. 
+ The solvent should not react with the compound being purified. The
desired compound may be lost during recrystallization if the solvent reacts
with the compound.
+ The solvent should be volatile enough to be easily removed from the
solvent after the compound has crystallized. This allows for easy and rapid
drying of the solid compound after it has been isolated from the solution.
The slower the rate of cooling, the larger the crystals are that form. The
disadvantage of recrystallization is that it takes a long time. Also, it is very
important that the proper solvent is used. This can only be determined by
trials and errors, based on predictions and observations. The solution must
be soluble at high temperatures and insoluble at low temperatures. The
advantage or recrystallization is that, when carried out correctly, it is a very
effective way of obtaining a pure sample of some product, or precipitate.

The weight of the crystals was recorded at 0.17g. The percent

recovery was observed by taking the actual mass of the recrystallized
substance (crystals) and dividing it by the original mass of the substance
(Benzoic acid) and multiplying the total by a 100. The value that was
recorded for the percent purity is 34%. The percentage that was recorded is a
relatively low value and it means that the Benzoic acid compound contained
66% of impurities prior towards the recrystallization process. Despite the
low value of the percentage recovery, the 34% amount of the Benzoic acid
recovered was in fact pure based on the melting range observed in the
experiment.
Potential errors that may have happened in this experiment may have
been leaving the Benzoic acid solution for a long period of time on the hot
plate. Excessive exposure to the heat may have evaporated portions of the
solution. Another error would be the isolation of the impurities from the
solution. After the solution finished boiling and the impurities were visible,
the solutions were left to cool a little too long that crystallization occurred
Organic chemistry laboratory 12

around the impurities which resulted in a little solution to recrystallize. To

correct this mistake, the solution needs to be transferred right after the
solution finishes boiling.
From the figure 2, we can see that the melting point of unknown sample
is 159.7oC, which belongs to the range [158–160] of salicylic acid.
VI. CONCLUSION
Recrystallization is a procedure for purifying an impure compound in a
solvent. The method of purification is based on the principle that the
solubility of most solids increases with increased temperature. This means
that the more temperature increases, the more the amount of solute in a
solvent dissolved increase. The purpose of this experiment is to purify
benzoic acid through the process of recrystallization. The purity of the
Benzoic acid will be determined based upon the melting point.
VII. REFERENCES
Mohrig, J., Hammond, C., Schatz F, 2010. Techniques in Organic
Chemistry, 3rd Edition, pp. 183-196
Mason, G.F., 1905. The Occurrence of Benzoic acid Naturally in
Cranberries. J. Am. Chem. Soc. 27(5), pp 631-614
Vaduvescu, S., University of Hawaii at Hilo, 2010, Recrystallization of
Benzoic Acid, p.1.
"Recrystallization Technique." Recrystallization Technique -
[www.rhodium.ws]. N.p., n.d. Web. 
Organic chemistry laboratory 13

EXPERIMENT 3: THIN LAYER CHROMATOGRAPHY

I. ABSTRACT
Thin layer chromatography is a chromatography technique used to
separate non-volatile mixtures. There are two phases of TLC technique is
stationary phase and mobile phase. In this experiment, we just used silica-
gel plate as stationary phase. And by using different solvent which different
polarity, we can compare how solvent effect in the result. In simple
mechanism, this technique base on the polarity of samples and solvent which
we are used. In addition, we also used different methods to determine the
colorless compound in TLC plates after chromatography, each method has
their own advantages and disadvantages, so it is important that we can use
some of them to get the best conclusion. In this experiment, a plant extract
will be separated into fraction containing compounds of similar polarities.
The purpose of this experiment is to introduce and reinforce proper
techniques for performing a column chromatography and a thin lay
chromatography
II. INTRODUCTION
Chromatography is a large number of physical methods that are used to
separate or analyze a complex mixture. The general process is that the
chemical mixture is carried by a liquid or gas and is separated into
components as the solutes flow around or over a stationary liquid or solid
phase. Separation occurs when on component of the mixture adheres more to
the stationary phase than the others. There are many different types of
chromatography, such as: liquid, gas, paper, column, thin layer, etc. Some
applications of chromatography include testing the purity of a compound,
analyzing the components/content of a mixture, identifying a compound,
Organic chemistry laboratory 14

preparation for other types of chromatography or uses (such as isolating the

pur compounds from a mixture).
Thin layer uses a thin, uniform layer of silica gel or alumina (stationary
phase) coated onto a glass, metal or rigid plastic plate. The mobile phase is a
suitable liquid solvent or mixture of solvents. When the plate is placed in the
solvent the solvent will creep up due to capillary action. The plate is spotted
with analytes which creep up the plate with the mobile phase. More polar
solvents (such as ethyl acetate, acetone or methanol) will result in higher
retention factors and faster movement up the plate
Thin layer chromatography (TLC) is a solid-liquid chromatography
technique used to separate non-volatile mixtures. They have a stationary
phase (solid, or a liquid supported on a solid) and a mobile phase (a liquid
or gas). In experiment, the components of mixture are carried by the mobile
phase through the stationary phase. TLC is the basic method can be used to
help determine the number of components in a mixture, the identity of
compounds, and the purity of a compound. 
TLC consists of three steps: spotting, development, and visualization. In
spotting, capillary is used to load a small amount of the mixture to TLC
plate. 
Development: Put the TLC plate into a pool of a development solvent,
which then travels up the plate by capillary action. It is important that the
solvent level is below the lone with the spot on it. We must cover the beaker
before experiment because to make sure that the atmosphere in the beaker is
saturated with the solvent vapor. Saturating the atmosphere in the beaker
with vapor stops the solvent from evaporating as it rises up the plate. 
Mechanism: The surface of silica gel is very polarity and, because of the OH
groups, can form hydrogen bonds with suitable compounds around it as well
as van der Waals dispersion forces and dipole-dipole attractions. It tends to
hold the polar compound in the mixture and solvent (usually organic
compound) tries to move the non-polar compound along with it as it travels
up the plate. Different components in the original spot, having different
polarities, will move different distances from the original spot location and
show up as separate spots. Given two compounds that differ in polarity, the
more polar compound has a stronger interaction with the silica and is,
therefore, more capable to dispel the mobile phase from the binding places.
The less polar compound moves higher up the plate (resulting in a higher Rf
value). 
Visualization: as simple case is colored compound, the spots can be directly
observed after development. However, in the case of colorless, a
Organic chemistry laboratory 15

visualization method is needed. There are two methods which is use UV

light and iodine vapors. First, by short wavelength UV light, the light must
be held close to the plate to see the spots. A second method of visualization
is accomplished by placing the plate into iodine vapors for a few minutes.
Most organic compounds will form a dark-colored complex with iodine. 
III. MATERIAL AND METHOD
Materials: We use plant crude extract with five solvents are Hexane,
Chloroform, Methanol, Petroleum ether, and Acetone in five vials. In
addition, we need TLC plate which is silica gel. To observation and
detection of phytocomponents, 3% boric acid and iodine is used.
Preparation of plant extract: Amount of plant crude extract is put into the
vial then add 5ml of Methanol into this vial, mix well to make sure that all
crude extract is dissolve into solvent (we can use sonication). After that,
drop 5ml Hexane to vial that containing complex, shake well and by using
pipette, we took Hexane out. Continue until the hexane which put into the
complex has colorless. Then, placing all vials which contain methanol and
hexane to the hot water bath until they are dry. Using pipette to drop 2-3
drops of acetone into each vial. 
Analytical Chromatography of plant extract: Four eluents were prepared (1)
a 5 mL of 100% chloroform (2) 5mL of a 9:1 chloroform/methanol mixture
eluent, (3) a 5 mL of a 8:2 Petroleum ether/ acetone mixture eluent, and (4) a
5 mL of 5:5 petroleum/ acetone eluent mixture. The TLC plate was placed in
a small amount of four prepared eluents in separate beaker along with
filtered paper with covered by aluminum foil and observed/analyzed. For
each chamber we prepared two separated TLC plates. Ones used for 3%
Boric acid observation and another is used with iodine. In the silica gel
plates, draw a faint pencil line around 1cm from the bottom edge (original
line). Using a capillary loaded with the extraction in the vial. Each plate
should be even in size and not too large to prevent smears and disturbed
streaks. Drying them with the air. Waiting to the solvent reach the edge
(about 1cm) of the top of TLC plates. Remove the plate carefully. 
Observation and detection of phytocomponents: There are several ways to
observe the spots: by spray in the 3% boric acid and then heat this plate in
the alcohol flame; another way is that develop TLC plate into the iodine
tank, cover on the top of the tank with aluminum foil then leave it
undisturbed for 30 seconds.
IV. RESULTS
Organic chemistry laboratory 16

100 chloroform –iodine 100 chloroform- boric

Organic chemistry laboratory 17

9 :1-iodine 9 :1- boric

8 :2- iodine 8 :2- boric

5 :5- iodine 5 :5- boric

Organic chemistry laboratory 18

V. DISCUSSION
In this experiment, we used TLC technique to separate the mixture in
plant crude extract. This method based on polarity of the compound in
mixture. Difference compound have difference polarity 
 and so difference in retention factor. It also depends on the solvent we used.
We can use more solvent or can mix two or more kinds of solvent to achieve
an optimum polarity and we can choose the best one in TLC experiment. 
In the experiment which 80:20 of petroleum ether: acetone as solvent,
acetone is more polarity than ether so when we use high ratio of non-polar of
solvent, the pigments can be separated more effectively. This is because the
non- polar compounds easily associate with the solvent and are eluted. If we
increase the polarity of solvent, the association with the solvent decrease and
the compound in samples hold on the polar silica as longer period of time to
ensure effective separation. For this reason, when we increase the ratio of
acetone in solvent as 5: 5 petroleum ether: acetone. The polarity of solvent
will be increase then decrease the efficiency. 
After using TLC technique, some compounds are colorless so we
cannot detect the present of it. Therefore, a visualizing technique is needed
to observe TLC results. There are many kinds of technique in TLC stains
such as 254nm UV light, permanganate stain, iodine chamber or CAM stain,
etc. In the case with staining by UV light, the UV light excites a fluorescent
additive in TLC plate. Compounds screen some of the UV, making
fluorescence weaker. Sometimes, visible fluorescence is excited by UV
making a spot brighter, and so is colored differently than the background. A
compound must have a chromophore. Even then, this technique is NOT
sensitive for isolated alkenes and benzyl ethers. Fluorescence is often
excited in poly-conjugated compounds (benzophenone, antracene and so
on). When we stain TLC plates in the iodine chamber, the different
absorption of blown colored iodine based on this formula: 
2R-SH + I2 → R-S-S-R + 2HI 
This method works with alkanes. Thiols and phosphines will
immediately show up as white spots. And another method to determine the
colorless compound is spraying TLC plate with acid and heat in alcohol
flame. The high temperature will evaporate solvent and make spots colored.
Each method has advantages and disadvantages. Therefore, we must use
different methods to compare the results and achieve the best conclusion. 
VI. CONCLUSION
In this experiment, we use thin layer chromatography to determine the
compound in plant crude extraction. Its mechanism based on polarity of
solvent is used and samples. Different solvents give different in result. When
Organic chemistry laboratory 19

using stationary phase is silica-gel plate (polar compound), the lower

polarity of solvent is used, the higher effective of experiment. With some
compound are colored, we can easy determine by visual. However, other
compounds are colorless, it is necessary to use TLC staining technique to
detect them. 
VII. REFERENCES
Clark, J.. N.p.. Web. 28 Oct 2013.
<http://www.chemguide.co.uk/analysis/chromatogrmenu.html
“Material safety data sheet.” GeoTrust. ScienceLab. N.p.. Web. 25 Sep
2013. <http://www.sciencelab.com>.
Padias, A. B. . Making the connections a how-to guide for organic chemistry
lab techniques. 2nd ed. Hayden-McNeil Publishing, 2011
Organic chemistry laboratory 20

EXPERIMENT 4 : COLUM CHROMATOGRAPHY

I. ABSTRACT:
The purpose of this experiment was to utilize the technique of column
chromatography in order to separate various compounds from each other.
This particular experiment was performed in order to isolate the large
amounts of the individual components in pure form from the mixture of ink
and silica gel. The reason why this separation was feasible was due to the
fact that these two compounds do not have the same polarity, and so this fact
was taken advantage of in order to separate the two from each other. The
fractions after were taken will be ran TLC.
II. INTRODUCTION
Column Chromatography is another common and useful separation
technique in organic chemistry. This separation method involves the same
principles as TLC, but can be applied to separate larger quantities than TLC.
Column chromatography can be used on both a large and small scale. The
applications of this technique are wide reaching and cross many disciplines
including biology, biochemistry, microbiology and medicine. Many
common antibiotics are purified by column chromatography.
Chromatography separation depends upon the presence of flowing liquid
(mobile phase) which carries the materials to be separated into contact with
fixed, non-moving substance (stationary phase). In order for separation to
occur, each of feed components must have a different degree of affinity for
stationary an mobile phases. Components that are more weakly retained by
stationary phase will move through a chromatographic system more rapidly
than the stronger one.
III. MATERIALS AND METHOD:
1. Materials:
For preparation for the laboratory, we need ink, silica gel for the most
important resources. Then we also need some classwares to do such as 5
Vials, Capillary, 1 Cylinder 5 mL, 1 Weighing bottle, 1 Spatula, Silica plate
for TLC, Silica for column chromatography, Ethanol, Distilled water, 1
Forceps, 3 Glass pipet, 1 Beaker 100 mL, Cotton, Aluminum foil.
2. Methods:
Firsly, we mixed the ink with silica gel (the amount of silica gel should be
sufficient to make the mixture dry and light color). For prepared the column:
Organic chemistry laboratory 21

First, we took the piece of cotton on the bottom of the column which can
prevent the silica gel fall out of the column. (if the cotton is too much or too
tight, this can prevent the eluent from dripping at an acceptable rate.). Then,
we clamped the column on the ring stand and rinsed the inner side of column
with ethanol. We prepared the silica in initial solvent by pouring dry silica
into the beaker of eluent with ratio 1:2, poured this into the column carefully
for maximize the amount of silica. Next, we allowed the solvent drip into the
clean flask (make sure the solvent never run dry or the solvent should be
1cm higher than the surface of silica layer). For running the column, we
transferred the mixture of the silica gel and ink into the column. Then, added
more solvent if needed (make sure the solvent never run dry). Finally,
collected the fractions based on the different colors.
IV. RESULTS:
We collected 4 fractions which are different colors

Then we ran the TLC and got this spots

Organic chemistry laboratory 22

V. DISCUSSTION:
To compare the two techniques, TLC and Column Chromatography: TLC
is thin layer chromatography. The stationary phase is applied to a flat
surface. A sample is applied at one end and the mobile phase is allowed to
flow and move the sample across the thin layer. In column chromatography
the sample is applied to the top of the column and the liquid mobile phase is
allowed to flow through the column effecting separation of the applied
sample. TLC is useful for identification through separation. Column
chromatography is useful for preparative separations. The differences are not
clear cut if the thin layer becomes somewhat thick and/or the column
diameter becomes somewhat narrow. Hence the best way to compare and
contrast is to do both kinds of separations and compare and contrast the
results.
Column chromatography is gravity driven, so the more solvent on topof
the column, the faster the solvent travels down the column. The solvent
cannot fall below the stationary phase because the column will dry out,
making cracks and air bubbles, so the columnwill not run as well.
Choosing solvent system is the most difficult choice to make the most
important. In every organic chemistry laboratory, there is a range of solvent
to choose. Colum chromatography is normally carried out with a mixture of
two solvents as the mobile phase: one polar, one non-polar. Occasionally, a
Organic chemistry laboratory 23

single solvent can be used or a mixture of three solvents is needed. Through

the column chromatography, there are two things that keep in mind. Firstly,
the solvent level in the column should not be allowed to fall below the top of
the slurry. Next, the abrupt changes in solvent polarity might cause poor
separations.
VI. CONCLUSION:
Column chromatography is used to identify that drugs have purity or not,
use for quantity the impurities of material. It also use in diagnostic labs for
determine amount of drug present in blood, urine sample, etc.
VII. REFERENCE:

Organic Chemistry Laboratory Manual. Ho Chi Minh : International

University, HCMC, 2016.
Organic chemistry laboratory 24

EXPERIMENT 5: SAMPLE DISTILLATION

I. ABSTRACT:
We separated the two components from a mixture of different boiling
points by distillation. The principle of this method is based on the
evaporation and separation to separate and filter the mixture mentioned
above. In this distillation method, 1: 1 mixture of hexane and toluene is
used, where the boiling point of the hexane is lower than that of the other.
We constructed two graphs, one representing the change of boiling point
versus volume, the other showing changes in refractive index relative to the
volume of distillation. Pure products after collection would be subjected to
chromatography for monomer quality assay. After the product we have
toluene and hexane. This method is effective when it is possible to create a
fraction with different boiling diagrams for each sample obtained and the
increase in temperature between the fractions and the refractive index will
show less infection compared to the other fractions.
II. INTRODUCTION
Distillation is a process of separating and purifying liquid mixtures,
where one substance is separated from another by condensation and
evaporation. There are four methods of distillation: simple distillation,
fractional distillation, vacuum distillation and steam distillation. However,
we just concerned in the sample distillation. (1) The boiling point of a pure
organic liquid is a physical property of that liquid. It is defined as the
temperature at which the vapor pressure of the liquid exactly equals the
pressure exerted on it. Boiling points can be determined using the technique
of simple distillation. Simple distillation is a technique that is used to purify
a mixture of liquids or to obtain a boiling point of a pure liquid (2).
Essentially, the liquid is heated to boiling and the vapors condensed above
the boiling liquid.

The liquid is poured into a round bottom flask and attached to a

distillation head, and attached to a condenser. When heated, the liquid
evaporates, slightly in contact with the thermometer head, and the
temperature begins to rise. Burp at boiling point, temperature is stable and
most of the ingredients are distilled. In the condenser, the steam is cooled
and formed into liquid and then dripped into the container. (2) The
Organic chemistry laboratory 25

condenser was placed over the vessels, we collected the distillate. In

addition, the temperature before the distillate was dropped down, it depends
on the reflux level.

In this experiment, we practiced with toluene and hexane. They were

separated by simple distillation based on their different boiling point. Some
notices for this technique, the round bottom flask contacted with heat source,
so it was easy to break the equipment. Observed the thermometer frequently
and adjusted the temperature if needed.

III. MATERIALS AND METHOD:

Materials: The chemicals that we used are Toluene and Hexane.
Laboratory technician gave us equipment include Distillation apparatus with
thermometer, stand, 1 round-bottom flask 100 mL, heating mantle and water
pump, 1 water bath, 2 glass pipet, 2 cylinder 10 mL, 10 test tubes and rack,
aluminum foil, refractometer.
Methods: Firstly, we set up the distillation system by pouring 25mL of
hexane and 25 mL of toluene. The ring stand contacted with round bottom
flask, water bath is needed for supporting the flask. Heated the mixture, and
collected the very first 1mL of fraction. This fraction was measured its
refractive index. Then, 5mL of following fractions are collected. Note: the
Organic chemistry laboratory 26

temperature and refractive index for each fraction had to be recorded. The
distillation is complete when the distillation flask is almost empty and the
temperature starts to drop or fluctuate. Construct two graphs: one of boiling
point versus mL distilled and the other of refractive index versus mL
distilled.

IV. RESULTS:

Volume distillate versus refractive index

1.52
1.5
1.48
Refractive index

1.46
1.44
1.42
1.4
1.38
1.36
1.34
0 5 10 15 20 25 30 35 40 45 50
Total volume of distillate (mL)

Figure 1. The graph of volume distillate versus refractive index for the
simple distillation of a mixture of hexane and toluene

Volume distillate versus boiling point

60

50
Boiling point

40

30

20

10

0
0 5 10 15 20 25 30 35 40 45 50
Total volume of distillate (mL)
Organic chemistry laboratory 27

Figure 2. The graph of volume distillate versus boiling point for the simple
distillation of

V. DISCUSSION:
Simple distillation is the best used for separating relatively pure liquids
with large boiling differences or liquids with solid impurities.
Advantages Disadvantages
 simpler setup than the other  requires the liquids to have
distillation. large boiling point
 faster distillation times differences (>70oC)
 consumes less energy than  gives poorer separation than
the other distillation fractional distillation
 only works well with
relatively pure liquids
The solvent is used to separate the small amount of a high-boling product
from a reaction mixture, the residue should be transferred into the other flask
and then be continued distilling. If we use the first distillation to isolate the
mixture, the solvent may be contaminated which influence on our results.
VI. CONCLUSION:
Based on the different boiling point of the organic compound (in this lab,
we used toluene and hexane), we can separate the individual components by
collecting the fractions and measuring the reflective index. The more
accurate reflective index, the more volume of distillate that we collected.

VII. REFERENCE:
Organic Chemistry Laboratory, International University – VNU, HCM,
2017.
Organic chemistry laboratory 28

EXPERIMENT 6: REFLUX DISTILLATION

I. ABSTRACT
In this lab, we distill “coconut” by using technique reflux distillation. This success
this technique can be evaluated by no loss of liquid to form vapor. The purpose of this
experiment is that to introduce technique of reflux while isolating fatty acids and lipid
from coconut. In the experiment, flaked coconut was reflux with petroleum ether and
then we filter it to get solution which was put into rotary evaporator to achieve the
result after this experiment.
II. INTRODUCTION
Many organic reactions are unreasonably slow and can take an extended period of
time to achieve any noticeable effect so heating is often used to increase the rate of
reaction. However, many organic compounds have low boiling points and will
vaporize upon exposure to such high heat, preventing the reaction from proceeding in
full. To address this, heating under reflux is used. This refers to heating a solution
with an attached condenser to prevent reagents from escaping. Reflux system is
method which heat is given to makes the liquid form vapor, as the vapor rise it is
cooled to a liquid and allowed to return to the reaction pot. Liquid is heated and
became a vapor. As the vapor reaches to condenser, which is cooling mechanism, it
will become water run though the condenser. Water should enter the condenser at the
bottom, and exit at the top to make sure that flow of water is cooling in condenser by
cooling mechanism. In this way, we can maintain a reaction at the boiling point of the
solvent indefinitely without the loss of solvent, as long as the water in the reflux
condenser is cool enough to condense all of vapor. During processing, it is usually a
good idea to ensure that the heating mantle can easily be removed either by raising
the set up and using a laboratory jack or ensuring that the assembly can be lifted out
of the heating mantle. Reflux allows chemists to observe chemical reactions that
require a constant temperature, controlled conditions and substantial time. It can also
be used to separate the components of chemical compounds. Reflux is used on an
industrial scale in oil refineries, chemical manufacturing plants and natural gas
processing plants, and in the manufacture of high-quality alcoholic beverages.
III. MATERIALS AND METHOD
Materials: In this experiment, we used these materials: condenser, clamp, clamp
stand, tube, pump, ice, 250 mL round- bottomed flask, heat, foil, rotary evaporator.
In this experiment, we used following equipment: petroleum ether, flaked coconut.
Organic chemistry laboratory 29

Procedures: First, we put 15 gram of flaked coconut in 250 mL round- bottomed

flask then added 100 mL of petroleum ether. Link it with the condenser by a clamp
and clamp it with clamp stand. Connect pump with the condenser by small tube like
diagram below and use small foil to lock the top of the condenser (open end).
Then we put the heat below the flask and heat it. After 1h heated, we take the round
bottomed flask out of condenser and use filter paper to filter flaked coconut. Finally,
put filtered coconut solution into rotary evaporator to concentrate it.
Organic chemistry laboratory 30

IV. RESULTS
Collect the coconut oil solution into a vial

V. DISCUSSION
Reflux helps to complete the reaction and it can collect the pure liquid because this
process will continue with a loop until the most volatile components in the liquid feed
boil out of the mixture. This process also do their self and is a closed system until the
Organic chemistry laboratory 31

liquid feed boil out of the mixture so we don’t need to do much things. Simple distillation
is different because we can only use it to take liquid from solid or residue. It is also have
a system we must do by our hand more than reflux because the vapor is channeled to
condenser and the residue need to transfer in other flask. This process also can make a
not pure liquid because we just have the liquid with only temperature that we set up in the
beginning.
Reflux can use also for simple distillation in case of separate a liquid from solid and
residue and in this case, two methods are interchangeable. But if in the case to separate
two or three liquid, we must use reflux because it will give us a pure in any liquid. In the
other hands, simple distillation cannot help us to have a pure liquid like reflux and it is
also take a lot of times because we need to do 2 or 3 times. So I think in this case, these
two methods cannot use to replace each other.
VI. CONCLUSION
In this experiment, we used Reflux distillation for extract coconut oil from flaked
coconut by the vaporization of a liquid, relocation and condensation
VII. REFERENCES
"What is the purpose of reflux in chemistry?" Reference. N.p., n.d. Web.
“Experiment 6: Reflux distillation” Organic Chemistry Lab Manual. International
University HCMCVNU, 2016
Organic chemistry laboratory 32

EXPERIMENT 7: LIQUID-LIQUID EXTRACTION

I. ABSTRACT
Caffeine was extracted from tea by the use of solid-liquid and liquid-
liquid extractions. An acid/base liquid-liquid extraction took place in order
to force caffeine into the organic layer. A pure product of caffeine was
obtained. Caffeine was the final product. Many sources of error may have
occurred such as an incorrect calibration of the scales with which the
samples were measured and not “washing” the solution thoroughly enough
to obtain as much sample as possible.
II. INTRODUCTION
Tea is one of the most commonly used caffeinated beverages in the
world. The caffeine (C8H10N4O2) found in tea is a bitter, white, crystalline
methylxanthine and a member of a class of compounds known as alkaloids.
Caffeine also causes an increase in respiration and heart rate, as well as
nervousness and insomnia. Though caffeine has demonstrated to have
physical dependence, it is also capable of improving alertness, learning
capacity, and exercise performance (NCBI, 2013). Tea leaves, in which
caffeine is found, also contain acidic tannins, undecomposed chlorophyll,
cellulose, and pigments. In order to extract caffeine from tea leaves, caffeine
must be present as the free base (Amrita, 2013). In order to do so, the above-
mentioned acidic substances must remain water-soluble
Liquid-liquid extraction is the technique to separate compound based on
their relative solubility in various solvents. It is an extraction of a substance
from one liquid into another liquid phase. The simple, easy-to-use static
extraction method is widely used and very effective in the field of extraction
analysis.
A separatory funnel, also known as separation funnel which runs on the
concept of "like dissolves like" that we learned in chemistry engineering.
This means that if a compound is polar, then it can only be dissolved in a
polar solvent. Following this logic, a non-polar compound can only be
dissolved in a non-polar solvent. In a separatory funnel, there are two
phases, the aqueous layer is polar, and the organic layer is non-polar.
Because these two layers share a surface, any polar substances that were
initially in the solution will be pulled into the polar (aqueous) layer, and any
Organic chemistry laboratory 33

non-polar substances will be pulled into the non-polar (organic) layer. The
largest risk when using a separatory funnel is that of pressure build-up.
Pressure accumulates during mixing if gas evolving reactions occur. This
problem can be easily handled by simply opening the stopper at the top of
the funnel routinely while mixing. This should be done with the top of the
funnel pointed away from the body. When shaking, hold the stopper in place
or it can become dislodged causing the liquids to spill. To account for this,
simply hold the stopper in place with one hand. The solvent is the key to a
successful separation by liquid-liquid extraction. Less toxic (non-toxic), do
not mix the water, solubility of component in solvent, the percentage of
component that can extraction, density, vapor pressure, viscosity, interfacial
tension, etc
Liquid-liquid extraction has several applications in bioprocess
technology: fermentation and algae broths, removal of high boiling organics
from wastewater, removal of carboxylic acid, protein separation and
purifications, essential oil extraction, agricultural chemical extraction, food
industry applications.
The advantages of this process include its effectiveness towards
compounds with high boiling points even in low concentrations, azeotropic
mixtures (mixtures with points that when boiled, have the same composition
in vapor than initially, thus cannot be altered by simple distillation) and with
heat sensitive compounds like large organic molecules. Disadvantages are
the large consumption of possibly toxic solvent, which also when recycled in
the system requires costly equipment. Thus, right selection of the solvent in
achieving a sustainable process is required and creates challenges to the
large-scale industry implementation of the process.
III. MATERIALS AND METHODS
Materials:
In this experiment, the main material were tea leaves to produce caffein
extracted and some chemicals were also required as petroleum ether,
chloroform. Some equipment needed was seperatory funnels, round-bottom
flask, distillation apparatus, rotary evaporation.
Procedures:
Firstly, we weighted 25g tea leaves, and soaked in 150mL hot distilled
water. Yellow color of solution was obtained after 30 minutes. Then, we
Organic chemistry laboratory 34

added chloroform after waste was rejected, in the separatory funnel to ready
for separate them. Tea extract is above layer and the solvent is remained
layer. To ensure the caffein was dissolved in solvent we shake it several
times, we opened the stopcock to remove all solvent and continuously, next
15mL solvent was added and repeated 2 times. In the water bath we put the
Erlenmeyer containing caffein extracted solution to evaporation. After few
minutes, we got crude caffeine and need to purify it. Then, crude caffein was
transferred to a 50-ml beaker and we added 5ml of benzene. To dissolve the
caffein we heated it on a water bath. After that, we added 10 ml of petroleum
ether and boiled with the temperature in range of 60 and 900C. Finally, we
used filtration to filtrate and collect the product, washing them with 1ml
ether. Putting the filter paper containing caffein next to the window to dry it
and then was taken to determine melting point.

IV. RESULTS
The extract of caffeine

V. DISCUSSION
Organic chemistry laboratory 35

In this experiment, liquid – liquid extraction method was used to extract

caffeine from dried tea leaves. In this method, methylene chloride solvent
which was organic solvent plays a role as solvent to increase the separation
of two layers. Based on the different in polarity of compound, the high polar
materials tend to dissolved in high polar solvent and the reversed. In this
instance, caffeine is usually a polar substance, but it becomes significantly
less polar when it is in a basic solution. Therefore, it is soluble in methylene
chloride and suspends in the organic layer. During the liquid-liquid
extraction, when using separatory funnel, it was important that two-layer
mixture in the funnel is vigorously shaken to mix two layer to increase the
efficacy through the extraction. After the mixing, let the solution equilibrium
for 10 – 30 seconds before collecting wanted layer. Then, allowing the
solution pass through filter paperand letting them dry in air would lead to the
final product which was caffeine crystallization.
VI. CONCLUSION
Extraction of caffeine from tea leaves is a very important and widely
practiced process known as decaffeination or removal of caffeine, regardless
of whether the goal of extracting the caffeine is to consume a less
caffeinated product or a more concentrated one. In this experiment, caffeine
was isolated from black tea leaves by using solid-liquid extraction followed
by liquid-liquid extraction. Because of solute in organic solvent, caffeine
was mix with methylene chloride which was the good organic solvent for
this assay.
VII. REFERENCES
Wang, H. Dynamic microwave-assisted extraction coupled on-line
with clean-up for determination of caffeine in tea. [Online] 2011, 1490-
1495. www.elservier.com/locate/lwt.
Williamson, K and Katherine Masters. Macroscale and Microscale
Organic Experiments, 6th ed.; Brooks/Cole, 2011
Dews, P., O'brien, C., and Bergman, J. (2002) Caffeine: behavioral effects of
withdrawal and related issues. Food and Chemical Toxicology40, 1257–
1261.
Onami, T., and Kanazawa, H. (1996) A Simple Method for Isolation
of Caffeine from Black Tea Leaves: Use of a Dichloromethane-Alkaline
Organic chemistry laboratory 36

Water Mixture as an Extractant. J. Chem. Educ. Journal of Chemical

Education73, 556.
Robertson, D., and Curatolo, P. W. (1984) The Cardiovascular Effects
of Caffeine. Caffeine 77–85.
Organic chemistry laboratory 37

EXPERIMENT 8: FISCHER ESTER SYNTHESIS

I. ABSTRACT
Isopropylformate was synthesized by a method is that Fischer esterification
reaction from isopropyl alcohol and formic acid by reflux. The distillate of
Isopropylformate was collect as colorless liquid with pleasant aroma.
II. INTRODUCTION
The purpose of this experiment is the synthesis of esters. Esters are
the functional group containing the hydroxyl group of a carboxyl group,
which is replace by an alkoxy or aryloxy group. Esters are abundant in
nature and commonly volatile due to low boiling point. As such, esters are
acknowledged as they are biologically and industrially aspects. For example,
in cosmetic and perfumery industry, esters are used in the synthesis of
essential oils while, in nature, different esters are released by different
species as pheromone, and they are caused of the scents of fruits and plants.
There are many methods to synthesize esters, however, an efficient method
is Fischer esterification. It is the process of forming an ester by refluxing a
carboxylic acid and an alcohol in the presence of an acid catalyst. The
alcohol is present mainly in excess, which used as solvent. The catalyzing
agents are different acids such as sulfuric acid and tosic acid. A tetrahedral
carbonyl addition intermediate created amidst the process of esterification
tends to lose a water molecule to form the ester. The reaction is generalized
as below:

Ester can synthesize in the laboratory to make food, perfume, and candle
industries. One of example of an ester used in these way is isopropylformate
- a constituent of coffee, plum brandy, various mushroom and dwarf quince.
III. MATERIAL AND METHOD
First, we assembled the reflux apparatus and greased the joints of
vacumn grease. Then, we weight and mix 75ml acid (formic acid) and 75ml
alcohol (isopropyl alcohol) with 5ml sulfuric acid in the bottom flask. We
Organic chemistry laboratory 38

started the water circulating and bring the mixture to boil under reflux for 60
minutes.

Next, we dismatle the reflux and cooled off the solution. We clamped a
separatory funnel to a ring stand of the hood, reminded that stopcock had
been closed. Then, transferred carefully the reaction mixture to the funnel.
We appropriated the cold water about three times to continue the liquid-
liquid extraction. We shaked the funnel vigorously and allow the layers to
separate.

We dissolved 16 of sodium bicarbonate in 200ml of water to prepare a

saturated sodium solution and used it to wash the crude extract. Next, we
collected the washed solution and disposed the remained reaction products
Organic chemistry laboratory 39

while assembling distillation apparatus. Finally, we collected the distillate at

the boiling point of isopropylformate.
IV. RESULT

The product is a colorless liquid with pleasant ordor.

The percent yield is 63.2%
V. DISCUSSION
Esters that have fragant odours are used as a constituent of perfumes,
essential oils, food flavourings, cosmetics, etc. Esters are also used as a
organic solvent. Esters naturally occur in fats and oils are fatty acid of
glycerol. Thus, esters are very important in many aspects, especially,
through this experiment, we can know well about the methods that is Fischer
esterification and could practice to create the fragrant.
Methyl salicylate or wintergreen oil is an organic ester naturally produced by
many species of plants, particularly wintergreen. In the past, it was
commonly distilled from the twigs of sweet birch and eastern teaberry or
wintergreen, but nowadays, commercial methyl salicylate is now
synthesized.
VI. CONCLUSION
Organic chemistry laboratory 40

To sum up, the synthesis of isopropylformate was achieved an acid-

catalyzed Fischer esterification from formic acid and isopropyl alcohol by
reflux and liquid-liquid extraction.
VII. REFERENCE
"Esterifications." Organic Chemistry. Accessed May 26, 2017.
"FISCHER SPEIER ESTERIFICATION, ORGANIC SYNTHESIS ... -
OuLUMA." Accessed May 26, 2017.
Organic chemistry laboratory 41

EXPERIMENT 9: SOLVENT EFFECTS IN AN SN1 SOLVOLYSIS

REACTION A KINETICS STUDY

I. ABSTRACT
Reaction kinetics can be used to probe the validity of a proposed
mechanism. For each proposed mechanism, factors that should influence the
rate of attaining the transition state, and thus the rate of the reaction, are
identified. A simple nucleophilic substitution reaction, solvolysis of tert-
butyl chlorides in three different solvent systems, is used to illustrate the
technique. Mixture of organic are formed in the first two solvent systems
because the alcohols contain hydroxyl (-OH) group. With the acetone-water
mixture, only the water participates in the solvolysis reaction. In all off the
solvent systems, the inorganic product is HCl.

II. INTRODUCTION
In this experiment, we will do the solvolysis of tert-butyl chlorides with
the ethanol-water solvent system and comparing the time for each of several
solvolysis reactions to reach the same per cent of completion. This study is
just relative, so the exact percent of completion does not important as well as
all the reactions are carried to the same point. When adding a measured
amount of NaOH to each reaction mixture, each mixture reamains alkaline
until the NaOH has been neutralized by the HCl being generated. The signal
that the mixture become acidic is when the solution change from pink to
colorless. We can compare the effects of various solvent systems upon the
rate of the SN1 reaction base on the percent water in each solvent system
versus the time required to reach the phenolphthalein end-point.

III. MATERIALS AND METHOD

First we determined that each test tube would had 2ml of ehthanol-
distilled water solution and we seperated this solvent by buret according to
the ratio :

Percentage Water (ml) Ethanol (ml)

(%)
50-50 1.00 1.00
45-55 0.90 1.10
40-60 0.80 1.20
Organic chemistry laboratory 42

35-65 0.70 1.30

30-70 0.60 1.40

Next, we corked the test tubes and placed them in the water bath with
a constant temperature for 5 minutes to come to thermal equilibrium. Placed
water at 30oC in 3 styrofoam cups, along with a thermometer. Then, we
added 3 drops of sodium hydroxide solution and 2 drops of phenolphthalein
to each test tubes.

To one tube at a time, we added 3 drops of t-butyl chloride and

shaked the contents of the tube immediately. Recorded the time of the
addition to the nearest second and keeped shaking continuosly. We waited
until the pink color dissappeared and recorded the time. During the course,
we remembered to maintain the temperature of water in the cups at 30oC.
Organic chemistry laboratory 43

IV. RESULT

The time that the

Percentage (%) solution turn into
colorless (minute)
50-50 0.185
45-65 0.190
40-60 0.272
35-65 0.288
30-70 0.752
Organic chemistry laboratory 44

V. DISCUSSION
In a concurrent experiment where the percentage of water in mixture was
changed, the data indicated a rate constant was also changed. This meant
that the reaction proceeded faster in water mixture because the mixture
contained higher proportion of the polar water. This is consistent with the
prediction that more polar solvent is more effective in stabilizing the
carbocation and halide ion in the intermediate stage. According to the
Hammond Postulate, lowering the energy of intermediates will lower the
energy of the transition state because the transition state is close to the
intermediates in energy. This will in turn lower the activation energy, and
the reaction would proceed faster. This effect of solvent polarity on
solvolysis of alkyl halides was also shown in another study where lower
percentage of ethanol in water mixture yielded greater rate constants for
solvolysis of t-butyl chloride.

There were indeed some errors in the experiment. Sometimes the

isopropanol mixture was slightly over-titrated as shown by the presence of
dark pink color at the end of the titration. This led to overestimating the first
Organic chemistry laboratory 45

order rate constant for the reaction. Also, there was a discrepancy in titration
endpoint, which makes the data less reliable, but again, this cannot entirely
account for the difference in rate constants.

VI. CONCLUSION
Thus, the solvolysis of t-butyl chloride in ethanol-water solvent system is
achieved a collection of time in each ratio of solvent. Through that we can
see the needed time for pink color of solution disappears is inversely
proportional to the amount of distilled water in each test tube. It means the
less amount of water, the longer time for reaction completes.

VII. REFERENCE
"Study of the Kinetics of an SN1 Reaction by Conductivity ..." Accessed
May 27, 2017.

"Experiment8-AmherstCollege."AccessedMay27,2017.

Swain, C. G.; Mosely, R. B. J. Am. Chem. Soc. 1954, 77, 3727.

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