SEMESTER II 2020/2021

CHM3102: ORGANIC CHEMISTRY

NAME DINIE ADLIN SYIFA BINTI ANUAR

MATRIC NO 206135
PARTNER’S NAME ARMAN AKRAM BIN OMAR

MATRIC NO 206113
NO OF EXPERIMENT 3

TITLE OF EXPERIMENT EXTRACTION OF ORGANIC MIXTURES

DATE OF EXPERIMENT 9 APRIL 2021

DATE OF SUBMISSION 16 APRIL 2021

LECTURER’S NAME DR NOR AZAM BIN ENDOT

DEMOSTRATOR’S JOSHUA CHEW INGKEAT

NAME
NOR NAJWA BINTI ZAINUL ARIFFIN
 Objectives :

A mixture that containing two solid organic compounds was separated.

The compound was isolated by using distillation process.
Melting point of solid was measured.
Background :
This experiment is about organic mixture that containing triphenyl carbinol and benzoic acid
that was soluble in ether. By extraction of organic mixtures, you want to separate a
reaction mixture or to isolate an organic substance from its natural source by water soluble salt
which is sodium benzoate. Separation of a mixture containing an acidic and a neutral compound
by using the separating funnel. Aqueous layer being drained out first into conical flask and
NaCHO3 added to the separating funnel to repeat the extraction then also draining the aqueous
layer combine into the previous aqueous layer. Leave a bit aqueous layer behind when pour into
conical flask at first time for the next extraction process.
Ether layer pour into conical flask and Na2SO4 added to it for drying process in 15 minutes.
The round bottom flask being weighed first and proceed to distillation process which is use to
isolate compound. When different compounds in a mixture have different boiling points, they
separate into individual components when the mixture is carefully distilled. We need to distilled
off the ether completely to recover the triphenyl carbinol. The weight of the round bottom flask
after distillation obtained and from that, the weight of triphenyl carbinol obtained and also it’s
melting point.
The aqueous layer that separated before constant stirring with the addition of dilute HCl until
the solution becomes acidic and it’s acidity being test on the blue litmus paper. Before filtration,
the filter paper being weigh first. Filtration the solution using the Buchner funnel will produce
white precipitate and being wash with small amount of water. Then, dry it on the vacuum pump
and weigh the filter paper. From that, we can obtain the weight of benzoic acid recover and also
it’s melting point.
 Data and Results :

Results Benzoic acid Triphenyl carbinol

Weight of compound in mixture (g) 0.6 0.4

Weight of compound recovered (g) 0.602 – 0.338 = 0.264 65.470 – 64.887= 0.583

Percentage of recovery (%) 0.264 0.583

× 100 %=44 % ×100 %=145.75 %
0.6 0.4
Melting point (º C) 124 160

Ether layer that contained triphenyl carbinol :

*The weight of dry round bottom flask = 64.887g
*The weight of bottom flask contained triphenyl carbinol = 65.470g

Aqueous layer :
*dilute 2M HCl to the aqueous layer until become acidic(blue litmus paper turn into red or
pink)
*the acidic aqueous layer is placed in the water bath & stirred slowly to from precipitate
*weight the filter paper first before use it on Buchner funnel & also wet it first with cold water
*dry in the vacuum pump to make sure there is no water left
*Weight of filter paper(before) = 0.338g
*Weight of filter paper(after) = 0.602g

Discussion :

In this experiment, we were separated the mixture(ether solution) that contained 0.6g of
benzoic acid and 0.4g of triphenyl carbinol by using the separating funnel which is involved the
extraction process. Extraction is a process of transferring a solute from one solvent to another
which it is used to separate one or more components from the mixture. For the first step in this
experiment is the separation of organic mixtures in order to separate the compounds and ended up
by two layers which is ether and aqueous layer in the separating funnel. Ether layer at the top
while the aqueous layer at the bottom since ether is less dense the aqueous. Next, the experiment
proceed to work up of the ether layer which at the end we got the weight and melting point of the
triphenyl carbinol. The round bottom flask was used to determine the weight of triphenyl carbinol
and the weight of bottom flask before distillation is 64.887g while the weight after distillation is
65.470g which means the weight of triphenyl carbinol that obtained is 0.583g. Through the
distillation, ether was distilled off completely and the solution become dry completely then the
recovery of triphenyl carbinol obtained and also the melting point measured is 160oC with the
percentage of the recovery is 145.75%. For the work up of aqueous layer part, based on the data,
we weighed the filter paper before filtration (0.338g) and after the filtration is 0.602g which is in a
dry state. From that, we got the weight recovery of benzoic acid (0.264g) and also it’s melting
point which is 124oC.

Extraction process is accomplished by shaking a solution in a separatory funnel with a solvent

that is immiscible(describe two phases that do not dissolved each other) with the one in which the
desired substance is dissolved and more soluble. After shaking the separating funnel, release the
carbon dioxide by opening the tap into the open space and continue shaking until no more CO2 is
formed. Two liquid layers are formed which can be separated from each other by draining the
lower layer through the stopcock of the separatory funnel. A mixture of benzoic acid(slightly
dissolved in cold water) and triphenyl carbinol can be separated with dissolve the mixture in the
separating funnel and NaHCO3 was added which react as a base and react with benzoic acid to
form a water-soluble salt while the triphenyl carbinol being a neutral which is remains in the
ether. After that, the aqueous layer can be separated from the ether layer by opening the
separatory funnel’s stopcock and draining the aqueous solution into a separate container(conical
flask). Leave a bit aqueous layer behind when pour into conical flask at first time for the next
extraction process. Proceed to the ether layer that has been separated into conical flask, Na2SO4
was added, the salt crystallizes by absorbing the water in the solution, leaving the solution free of
water and isolating the triphenyl carbinol. Distillation of the ether will identify and purify the
organic compound(triphenyl carbinol) which the compound separated by exploiting their boiling
points and the mixture being separated into its component parts when it is distilled. The recovery
triphenyl carbinol obtained and the melting point will be measured. For the work up of aqueous
layer, HCl was added to the aqueous solution because HCl can get that acidic compound back
since it is mineral acid. After we loss of acidic compound while work out of the ether layer and it
becomes ionic and water soluble when it loses a proton. So, only neutral compound leave. The
basic aqueous solutions are neutralized with concentrated HCl to form benzoic acid because it
insoluble and can form precipitate. It will work out by collected, recrystallized using the filtration
and allowed to dry on the vacuum pump to get pure benzoic acid and also it’s melting point
obtained. The melting point readings indicated that benzoic acid and triphenyl carbinol, which re-
crystallized was indeed pure and the melting point matched the known melting range of benzoic
acid and triphenylmethanol.
There are some errors that can affect the results of the experiment especially the weight of
the benzoic acid and triphenyl carbinol obtained. One of the errors is the layers obtained in
separating funnel are too little which is can affect the separation become not effective and because
of that, solvent will be add to solve this error. Next, after the flask that contained ether solution
was poured into the separating funnel, make sure to rinse the flask with ether and pour remaining
into the separating funnel which is to ensure that there is no loss of benzoic acid or triphenyl
carbinol. So, the recovery of the compounds that we get at the end of the experiment is acceptable
and more accurate. Other than that, the separatory funnel may, in fact, be damaged. Occasionally
a contaminate may become lodged in the stopcock. For this reason it is always good practice to
wash the separatory funnel before attempting extraction and checking to be sure it drains properly.
The common problem, however, is that the cap has been mistakenly left on the separatory funnel
while attempting to drain. This establishes a vacuum within the separatory funnel and will not
allow any liquid to drain.

Conclusions

 The separatory funnel runs on the concept of "like dissolves like", with different solutes
being preferentially soluble in certain solvents. While a separatory funnel is being shaken,
the two solvents mix and share a large surface area, which allows each solute to migrate to
the solvent in which it is more soluble. The solvents do not form a unified solution
together because they are immiscible. When the funnel is allowed to sit after being shaken,
the liquids form distinct physical layers, with the less dense liquid floating and more dense
sinking. A mixture of solutes is thus separated into two physically separate solutions, each
enriched in different solutes.
 Distillation process which is use to isolate compound. When different compounds in a
mixture have different boiling points, they separate into individual components when the
mixture is carefully distilled. We need to distilled off the ether completely to recover the
triphenyl carbinol.
 Melting point can be measured after the pure compounds obtained and it has own range
 melting point which it start from the compound begin melt until completely melting. Both
compounds shown that it’s melting point obtained consistent with their melting point
range.

QUESTIONS

1. Why do you use NaHCO3 in Section B?

-Because NaHCO3 will neutralize since it is basic compound by removing the acidic compounds.
This reaction will afford the carbon dioxide. When the pressure builds up, that will push some of
the gas and liquid out from the separating funnel.

2. What is the purpose of HCl in Section C?

- Because HCl can get that acidic compound back since it is mineral acid. After we loss of acidic
compound while work out of the ether layer and it becomes ionic and water soluble when it loses
a proton. So, only neutral compound leave. The basic aqueous solutions are neutralized with
concentrated HCl to form benzoic acid and triphenyl carbinol because it insoluble and can form
precipitate. It will work out by collected, recrystallised and allowed to dry to get pure benzoic
acid.
3. During the distillation, why do you use water bath for heating?

- Because it can reduce the chance of boiling alcohol due to mistake with temperature or boil
time. The alcohol contained in the solution can be remove by it. The water bath use to transfer
water temperature to resistance value.