UNIVERSITI TEKNOLOGI MARA, CAWANGAN PERLIS

KAMPUS ARAU

LABORATORY REPORT
CHM 457
ORGANIC CHEMISTRY

EXPERIMENT 1 : ACID-BASE EXTRACTION

DATE : 30 APRIL 2020
GROUP MEMBER : LIYANA SYAKIRAH BINTI HASHIM
(2020993211)
NOOR NASUHA BINTI NOOR ARIFFIN
(2020996489)
NUR ALIYYA SYAKIRIN BINTI
SHAHARUDDIN (2020963781)
GROUP : AS245_2B
LECTURER : SYARIFAH NURSYIMI AZLINA SYED ISMAIL
EXPERIMENT 1 : ACID-BASE EXTRACTION
Objective :
1. To verify that the acid impurity has been removed completely from the ether layer

Introduction :

Acid-base extraction is a method that is commonly used to separate a mixture of organic

compounds from each other based on their acid-base properties. This method is also called
liquid-liquid extraction. From the reaction to produce a neutral compound, the product
usually contaminated by an acid or base impurity. Therefore, by performing acid-base
extraction, the neutral compound can be isolated from the acid or base impurities.
Considering organic acids and bases will become ions in acid-base reaction, the neutral
compound should be mixed with mineral base or acids in order to dissociates the acid and
base impurities. In this experiment, an unknown neutral compound that has acid impurities is
dissolved in organic compound which is ether before performing several procedures to
eliminate the acid impurities. Then, the mixture of organic compound and neutral compound
is mixed with sodium hydroxide and is shaken in the separatory funnel to dissolve the acid
impurities. The aqueous layer is then separated from the ether layer containing the neutral
compound.

Procedure :
1. 0.24 g of unknown sample and 0.12 g of benzoic acid was weight and placed in
centrifuge tube.
2. 10.0ml of ether was added to the centrifuge tube and cap it
3. The tube was shaked until all the solid dissolves completely
4. The solution will then be transferred into a 125ml separatory funnel.
5. 5.0ml of 1.0M NaOH was added to the separatory funnel and shaked it for 30
seconds
6. After 30 seconds, drain the bottom aqueous layer into the Erlenmeyer flask and
labeled as first NaOH extraction
7. Another 5 mL of the 1M NaOH solution was added to the ether layer in the
separatory funnel and steps 1-6 was repeated. Labelled the second aqueous layer in
a different Erlenmeyer flask as second NaOH extraction
 8. By using a glass rod, slowly stirred while adding 6M HCl into each of Erlenmeyer
flask until the solution turns acidic. Use litmus paper to observe if the both solution
has turn acidic. (Blue litmus paper will turn red if solution is acidic)
9. The flask then was taken to cool in an ice bath for about 15 minutes or until
thoroughly chilled
10. The solid benzoic acid was collected using Buchner funnel and filter flask
11. 2-3ml water was used to wash and allowing the suction to continue for 5 minutes to
get solid as dry as possible
12. 5ml of saturated solution of sodium chloride was added to ether layer in separatory
funnel
13. Shaked the separatory funnel for 30 seconds and let the layers separate.
14. The ether layer was transfer into Erlenmeyer flask and dry the ether layer over
granular anhydrous sodium sulfate
15. Swirled the Erlenmeyer flask and leaved to stand for 10 minutes
16. While the ether layer was drying, a Erlenmeyer flask was weighed
17. The dried ether layer was transfer using Pasteur filter pipette into a Erlenmeyer
flask
18. The Erlenmeyer flask then brought to steam bath in the fume hood to evaporate the
ether
19. After evaporated, the Erlenmeyer flask was cooled at the room temperature and was
reweighed to determine the amount of solid solute that was in the ether layer
20. The melting point was obtained and compared to the chemical given

RESULT :
Melting point of benzoic acid : Unable to determine because no sufficient amount of solid to
be tested.
Melting point of unknown sample : 163℃
We can identify the unknown sample is triphenylmethanol because the range melting point of
triphenylmethanol is 162℃ - 164℃.

DISCUSSION:

In an effort to learn the extraction of an acid-base mixture, we conducted an experiment that will
separate a mixture of an acid, base and a neutral compound into its individual components. In addition
we learned how to purify the unknown sample by recrystallization as well as identifying the
compound by using melting point determination. The extraction of benzoic acid is made possible
because the addition of sodium hydroxide NaOH. The base will react only with the carboxylic acid in
the mixture, thus forming a water soluble salt. Since the base of sodium hydroxide added will
deprotonate the benzoic acid, the HCl added will reprotonate the benzoic acid causing the benzoic
acid to be restored as neutral and thus precipitates out. The order of extraction started with benzoic
acid substance as it has a higher density and is the first layer that was drained out from the separatory
funnel. The melting point reading indicated that benzoic acid was indeed pure and the melting point of
1220C matched the known melting range of benzoic acid. However, we did not perform the melting
point determination for 1 st NaOH extraction as we were not able toget adequate precipitate. Whereas,
we recovered the same as 1st extaction. We might have made a mistake when draining out the 1st and
2nd NaOH extraction by accidently draining the ether layer along with it. Since benzoic acid is
soluble in ether, this might be the reason as to why the precipitation we accumulated for benzoic acid1
and benzoic acid2 is a very diminutive amount. The unknown sample was determine by using melting
point apparatus, in which the sample is filled inside a capillary tube and inserted into the instrument to
determine the melting point. The results came out with the sample possessing a melting point of
163C. From this we compare the sample’s melting point with the lists of various compounds’ melting
point provided in the lab manual. Since the compound triphenylmethanol’s melting point ranges from
162C - 164C, our unknown sample’s melting point lies between the stated range, therefore we
concluded that the unknown sample is triphenylmethanol. The weight of the unknown sample
recovered is unidentified due to insufficient. Hence, we were not able to calculate the percentage
recovered of the unknown sample by using this formula,Supposedly, to be observed that both benzoic
acid solution produces white precipitates and can be seen clearer after filtration and drying process.
However we were not be able to identify due to absence of precipitate.rates

CONCLUSION :

From this experiment, the acid impurity from the unknown solution is separated by liquid-
liquid extraction method. The acid impurities from the organic mixture are separated by
dissociation when the NaOH solution is added in the mixture of organic compounds and
neutral compound. Then, the ether layer was added with saturated aqueous sodium chloride
solution to remove the aqueous layer. The ether layer was then dried to obtain the mass of
solid solute that was in the ether layer and the melting point of the solid was determined.

REFERENCE: 
WEB: https://www.khanacademy.org/science/chemistry/acids-bases-topic  WEB:
https://www.britannica.com/science/acid-base-reaction  BOOK TITILE: Acid-Base Extraction
AUTHORS: Frederic P.Miller, Agnes F. Vandome, McBrewster John PUBLISHER: VDM
Publishing, 2010