OBJECTIVES OF THE EXPERIMENT

1) To separate the mixture of acid, base and a neutral compound into its individual
components.
2) To analyze and identify the compound by melting point determination.

INTRODUCTION
Extraction involve the dissolving method of a compound from a solid into solvent
or from a solution into another solvent. Extraction used to wash the solution of organic
solute in an organic solvent that free from impurities. Acid base extraction is a one of
the type of liquid-liquid extraction. Acid-base extraction involve the different levels of
solubility levels in water and an organic solvent. The uses of acid-base extraction is to
separate the organic compounds from each other based on their own properties. The
differences of acid and base are any substances that have pH value between 0 up to
7 will be considered as acid solution. For base when the pH value occur within 7 to 14
it will be considered as basic. A requirement of a solvent-solvent extraction is the two
solvents must be mostly insoluble into each other.
In this experiment, a mixture that consist of an acid (benzoic acid) will be
separate from a neutral compound. The neutral compound are triphenylmethanol or
1,2,4,5,-tetrachlorobenzene. The mixture of this solution dissolved in diethyl ether.
The mixture of the two solvents must be separates into two layers. It is very important
to note that upper layer is less dense than the bottom layer. NaOH used for extraction
because of the increased evolution of heat during the extraction and potential side
reactions with the solvent. A strong base like NaOH or NaHCO3 used to remove an
acidic compound from a mixture.

MATERIALS
O.24g unknown, 0.12g benzoic acid, 10.0 mL ether, 10.0 mL of 1.0 M NaOH, 6 M
hydrochloric acid, 5 mL saturated NaCl and sodium sulfate.

APPARATUS
125 mL Erlenmayer flak, 125 mL separatory funnel, weighing balance, litmus paper,
test tubes, measuring cylinder, warm water bath, pasteur pipet and melting point
apparatus.
EXPERIMENTAL PROCEDURE
0.24g of unknown and 0.12g of benzoic acid were added to a centrifuge tube.
10.0 mL of ether were added to the tube and capped it. The tube was shaken until all
the solid dissolved completely. The solution were transferred into a 125 mL
separatory funnel. Then, 5.0 mL of 1.0 M NaOH were added to the separatory funnel
and shaken for 30 seconds. The layers were separated. The bottom (aqueous) were
removed and placed in the Erlenmeyer flask and labeled as “1st NaOH extract”.
Another 5.0 mL portion of 1.0 M NaOH added to another funnel and shaken for 30
seconds. When the layers separated, the aqueous layer were removed and put in
Erlenmeyer flask and labeled as “2nd NaOH extract”
6 M HCl added drop wise to each of the two test tubes that contained NaOH
extracts until the mixture were acidic. The mixture were tested with litmus paper to
determine when they are acidic. The amount of the precipitate observed. To the ether
layer in the separatory funnel, 5.0 mL of saturated aqueous sodium chloride were
added. The solution were shaken for 30 secondhand the layers were separated.Then,
the aqueous layer were discard and removed. The ether layer poured from the top of
the separatory funnel into a clean and dry Erlenmeyer flask. The ether layer dried over
granular anhydrous sodium sulfate. The dried ether solution were transferred to a dry
Erlenmeyer flask and preweighed the flask. The ether were evaporated by heating the
flask in a warm water bath. When the solvent been evaporated, the flask was
removed from the bath and dried outside the flask. Once it cooled to room
temperature, the flask was weighed to determine the amount of solid solute that was
in the ether layer. The melting point of solid were obtained and identified according to
the given table.
RESULTS
Actual weight of benzoic acid = 0.214g
Weight of benzoic acid recovered = 0.0535g
Observed melting point of benzoic acid = 121℃
Percent recovery of benzoic acid = 25%

Actual weight of unknown sample = 0.242g

Weight of unknown sample recovered = 0.1131g
Observed melting point of unknown sample,
Triphenylmethanol = 162℃
1,2,4,5-tetrachlorobenzene = 140℃
Percent recovery of unknown sample = 46.74%
DISCUSSION
An acid-base extraction performed through a series of filtration and separation
method. All the compounds in the mixture dissolves in ether solution but insoluble in
aqueous layer until further conditions allowed to soluble. This is because water is poor
solvent of covalent molecules. One of the reason why a strong base like NaOH used
in this extraction is to remove an acidic compound from a mixture. After the addition of
NaOH, there was immediately a clear separation of the layers because the solution
were immiscible.
From the results obtained, the melting point of unknown sample are 140℃ and
162℃. According to the table given, 140 ℃ are placed at the range of
1,2,4,5-Tetrachlorobenzene which is between 139 ℃ -142 ℃ . For another value
obtained, is goes to Triphenylmethanol which equal to 162 ℃ because it is in the
range between 162℃-164℃. For benzoic acid, the observe melting point for benzoic
acid are 121℃ which produce the least melting point. The percent recovery for
benzoic acid and unknown sample are 25% and 46.74% respectively.
The errors that were identified during this lab session are inaccurate separation of
the liquid layers and rapid recrystallization. Precipitate were not completely filtered out
from the solution. The small percent recovered of benzoic acid may caused from the
inaccurate actual weight of benzoic acid. This is because of the plate of weighing
balance have the excess solid left by the previous users. In the drying process, there
is a mistake done which is the products are left over around the Buchner funnel that
decrease the weight of benzoic acid recovered. To minimize the errors student should
be more careful in order to pour the ether layer into the Buchner funnel. This
experiment enhance the skills on how to separate the mixture of an acid and a neutral
compound. It also increase the skill on how to pipette a specific layer out of solution to
become more accurate.
CONCLUSION
As the conclusion it can be conclude that, the mixture that consist of acid, base
and neutral compound were successfully separated to its individual components. The
percent recovery of unknown sample are 46.74% and the melting point for unknown
sample are 140℃ and 162℃.Acid-base extraction is an example of solvent-solvent
extraction which used in industries.

QUESTIONS
1) List 4 water-immiscible liquids other than ether that could be used to extract
organic compounds from aqueous solution.
Chloroform, cyclohexane, dichloromethane and carbon tetrachloride

2) Why it is wrong to leave a bottle of anhydrous sodium sulphate or calcium chloride

open?
The air contains of water which it expose the anhydrous to absorb the water particles
in the water and effect the effectiveness.

3) Draw the structure of the product when benzoic acid react sodium hyroxide. Why is
the product of this reaction easily extracted into H2O, while the original benzoic acid is
not so easily extracted into H2O?
OH removed H+ to form a salt. The polar salt is soluble in aqueous solution. OH
and benzoate are bases. The stronger base takes H+ to form the weaker base.

4) Why does benzoic acid precipitate out when the aqueous layer is acidified with
HCl?
This is because benzoic acid is a stronger base compared to Cl . So it will take H+
from HCl and precipitate out of the solution.

5) Develop a procedure for isolating a neutral compound from a mixture containing a

basic impurity by drawing a flow chart?
 ether

Naphthalene trace of NaHCO3

Water
ether

naphthalene Small amount of

NaHCO3

Dry sodium Discarded

sulphate
napthalene

REFERENCES

1) https://study.com/academy/lesson/acid-base-extraction-theory-purpose-procedure.html
2) http://www.chem.ucla.edu/~bacher/Specialtopics/extraction.html
3) https://frtr.gov/matrix2/section4/4-15.html
4) https://people.chem.umass.edu/samal/267/owl/owlextract.pdf
5) https://www.thevespiary.org/rhodium/Rhodium/chemistry/extraction_theory.html