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Experiment 1: Acid-Base Titration


The purpose of this experiment is to learn the proper techniques of acid base extraction. Besides
that is to identify the unknown sample and the melting points of the unknown sample and
benzoic acid.


Nature’s liquids are solutions and her solids are usually mixtures. It is no wonder that so much
research has gone into the development of separation process. One of the best of these, and one
with limitless versatility, is extraction.

This experiment is the technique for the separation of mixture of acid, base, and neutral
compounds. In the procedure, the solution is altering the solutes to accommodate the solvents,
and the separation efficiency becomes almost quantitative.

As a general rule, monofunctional organic compounds having more than five carbons tend to be
ether soluble and water insoluble. Salts and polyfunctional compounds have the reverse
solubility characteristics. They tend to be water soluble and ether insoluble. This extraction
technique is used for the separation of the mixtures. The mixture is dissolved in ether. First the
amines (organic base) are converted to water-soluble salts with HCL and are extracted in the
water layer. Next the organic acids are neutralized to water soluble salts with NaOH and
extracted in the water layer. Finally, only the neutral compounds remain in the ether and can be
recovered by distilling off the ether.

The basic aqueous solution is neutralized with concentrated HCl to yield the carboxylic acid,
which, because of its water insolubility, precipitates out. This can be collected, recrystallized and
allowed to dry to yield pure carboxylic acid.

Chemicals required:

0.24 g of an unknown (Triphenylmethanol or 1,2,4,5-tetrachlorobenzene)

10.0 ml ether
10.0 ml of 1.0 Naoh
6 M HCl
5.0 ml saturated Nacl
Na₂SO₄ anhydrous

125ml Erlenmeyer flasks

125ml separatory funnel
Weighing balance
Hot water bath/steam bath
Melting point apparatus
Litmus/pH paper
Pasteur pipets


First extraction

1. 0.24 g of unknown sample and 0.12 g of benzoic acid was weigh and they are placed in
test tube.

2. 10 ml of ether was added to the mixture and then it was shake to dissolve the mixture.
Then the solution was transferred to the separatory funnel and 5 ml of 1 M NaOH was
added later on.

3. It was cap tightly and the layer was mix by swirling and shaking it gently for 30 second.
The pressure inside the separatory funnel was vent out by tilting the funnel and then
opening the stop cork.

4. The process of removing the pressure was repeated for couple time.

5. Then the mixture was let to stand on its own to allow the layers to separate. The top layer
is ether and the bottom layer is aqueous layer.

6. The aqueous layer than was drained to Erlenmeyer flask and it was labeled as first
extraction of NaOH.

Second extraction

1. Another 5 ml of 1M NaOH solution was added to the other ether layer in the funnel and
the above procedure was repeated for the second extraction step.

2. Then the aqueous was transferred to the other Erlenmeyer flask and it was labeled as
second extraction of NaOH.
3. The flask then taken to the hood and 6 M HCl was added slowly into each Erlenmeyer
flask with the guidance of glass rod until the solution become acidic. The solution will
become acidic when it changed the blue litmus paper to red.

4. Then it was cooled down in ice bath for about 15 minutes or until it thoroughly chilled.
The solid benzoic acid was collected by using Buchner funnel and filter flask. 2-3 ml of
chilled water was used to wash it and the suction was allowed to occur in 5 minutes to get
the solid as dry as possible.

5. Then it was gently scraped into watch glass and the drying process was continued in the

6. The solid was weigh and the melting point was obtained. By assuming exactly half of the
original mixture was benzoic acid, the percent of recovery was calculated.

Preparation of drying agent

1. 5 ml of saturated sodium chloride was added to the ether layer in separatory funnel to
remove any trace of NaOH solution.

2. Then it was capped, mixed and vent to let the layers separated as before. The aqueous
layer then discarded.

3. The ether layer then transferred into Erlenmeyer flask and 1 g of anhydrous sodium
sulfate was added to remove moisture it contained. Cork the flask then swirl it and it was
let to stand on its own for 10 minutes.

Determination of unknown compound

1. A small dry beaker was obtained while waiting for ether to dry.

2. The dried ether layer then transferred to the beaker with a clean Pasteur filter pipet.

3. The ether was carefully evaporated in steam bath inside the fumehood.

4. Then when all ether has evaporated, the beaker was cooled at room temperature; it was
dried and reweighs it to determine the yield of unknown sample.

5. A small amount of it was scraping out and their melting point was obtained for the two
chemicals given.

6. The unknown neutral compound was determined. The percent of recovery was calculated
by assuming that exactly half of the original mixture was the unknown neutral compound.

Weight of filter paper: 0.6182g

Table 1: results of the experiment

Title Result/observation
Actual weight of benzoic acid 0.1203g
Weight of benzoic acid 0.0848g
Melting point of benzoic acid 160 oC
Actual weight of unknown sample 0.2423g
Weight of unknown sample recovered 1.215g
Percent recovery of unknown sample 134%
Melting point of unknown sample 122oC

Table 2: observation in the reaction

Benzoic acid extraction -The solution forms two layers after adding the
mixture of benzoic acid, unknown compound
and 5mL of NaOH.
- The solution becomes acidic when 6M HCL
is added. The blue litmus paper turns to red
- After cooling process some benzoic acid is
precipiting out.
unknown extraction -the ether layer from the first extraction is
continuous to mix with the 5mL of NaCl and
form the two layers.
- The ether becomes dry when the anhydrous
sodium is added. Also after evaporation and
cool at the room temperature, the ether is dry
so that it can easily scrape out the small
amount of it.

a) Benzoic acid:

Actual mass of benzoic acid= 0.1203g

Mass of filter paper= 0.6182g

Mass of original mixture= mass after dried – filter paper

= (0.7030-0.6182)g

= 0.0848g

% of recovery:

= Mass of benzoic acid recovered X 100%

Actual weight of unknown sample

= 0.0848g x 100%


= 70.49%

b) Unknown neutral compound recovery:

Mass of unknown sample recovered

=weight after cool at room temperature – weight of conical flask

= 75.680g – 75.355g

= 0.325g

% of recovery:

=Mass of unknown sample recovered x 100%

Actual weight of unknown sample

= 0.325 x 100% = 134%



The expectation by doing this experiment is to make sure that half of the original mixture is the
unknown compound. However, after done this experiment the percentage on yield might slightly
lower than expected.

By obtaining the melting point, the unknown sample can be categorized as either
triphenylmethanol- 163oC or 1,2,4,5- tetrachlorobenzene- 140oC. Compared to the melting point
obtained from the experimental, for the unknown sample is 160oC. So the unknown compound
can randomly categorize as triphenylmethanol compound. For the observation of the melting
point of benzoic acid is 122oC.

Nevertheless, the percentage on recovery the unknown sample that obtain is 501%, is different
with the expectation at the earlier at the experiment. The reason by how the percentage on
recovery is lower than expected because difference of error is because of the technical limitation.
In order to determine the unknown sample in the ether, a dry beaker has been used to transfer the
dried ether layer into the beaker. However, the using of Erlenmeyer flask instead of beaker does
affect the cooling and evaporation process. It might say that the narrow tube of the Erlenmeyer
flask can prevent the evaporation on the steam bath happened completely and also when the
Erlenmeyer flask is cooling at the room temperature the dried ether is not completely dry and it
still wet and the appearance looks like sticky. It can be assumed that insufficient steaming and
cooling do affect the percentage. Besides that the chemical on the bench can be contaminated to
the sample. Thus the final weight that obtain is together with the weight of accumulated with the
chemical from the bench. Thus it may affect to the percentage of the unknown sample.

The suggestion that can be applied to improve this experiment is by using an appropriate
apparatus so that it can ensure that all the heating and cooling process can be done completely.
Another way to prevent is do not put the sample on the bench and also wash the apparatus after
use it to avoid any mixing of chemicals that can be accumulated in order to determine the weight
of the sample.


At the end of this experiment, the percentage recovery of the unknown sample is 501%. The
melting point of benzoic acid is 160oC and the melting point of unknown is 122oC .The
difference of the percentage from the experimental than the expectation is because of the sort of
technical errors. The moral that can learned from this experiment is try to avoiding any personal
errors and use the correct apparatus for the right method instructions.


1. Arne langsjoen, Everett.W.G, Lieder.P, Lata.Y.A. 1988 Experiments in general, organic,

and biological chemistry. Harcourt Bruce Jovanovich, Orlando Florida.

2. McMurry.J.2003 Fundamentals of organic chemistry. 5th Ed. Thomson Brooks/ Cole. US.

Post Lab Question

1. 4 water immiscible liquids other than ether to extract organic compounds from aqueous


-Ethyl acetate


-Hexane and iso-octane are useful for non-polar solvents

2. Why is it wrong to leave a bottle of anhydrous sodium sulfate or calcium chloride open?

Is it wrong to leave a bottle of anhydrous sodium sulfate or calcium chloride open

because of it will absorb the moisture from the surrounding and therefore it will less
capability of sodium sulfate or calcium chloride to act as ‘ drying agent’

3. Draw the structure of the product when benzoic acid reacts with sodium hydroxide. Why
is the product of this reaction easily extracted into H2O, while the original benzoic acid is
not easily extracted into H2O?

OH + NaOH ONa + H2O

benzoic acid is not easily extracted into H2O because it is low solubility in water. But the
salt of benzoic acid which called sodium benzoate is easily extracted into H2O because it
has high solubility in water.

4. Why does benzoic acid precipitate out when the aqueous layer is acidified with HCl?

Benzoic acid is relatively insoluble in water even though there is hydrogen bonding. If
benzoic acid precipitates out, this means that either protonated or deprotonated benzoic
acid existed in the first place. When a strong base is added to an acid, it is
thermodynamically favorable for the acid to lose the proton to the strong acid. Or if an
acid stronger than benzoic acid is added to the solution, then the hydroxyl group is
protinated. Any molecule with a charge is soluble in water due to the polarity of water.