EXPERIMENT 1 : ACID-BASE EXTRACTION

Objectives

1. To separate the two compounds of your unknown mixture.

2. To analayze and identify the compounds by melting point determination.

Introduction

Acid / base is an extremely useful separation technique in organic

chemistry. Using simple acid/base reactions, several different classes of organic
molecules can be separated from one another.We will be randomly given a
mixture containing two components; an acid, a base, or a neutral component.
We have to separate the mixture by acid/base extraction, recrystrallize and the
solid compounds and identify them based on solubility and melting point
determination.

Nonpolar organic solvents are insoluble in water, therefore when it in

contact with water, they form a separate layer. This makes it possible to
separate things that are soluble in water from things that are soluble in nonpolar
solvents. These separations are called extracting and washing. Extraction and
washing are very similar – in fact, they involve the very same physical
operations. The difference is that when you extract something, you remove a
product from the mixture, leaving the impurities behind. When you wash
something, you remove unwanted impurities from a mixture, leaving the
product in the original solution. It is important to keep track of where the
desired product is and it could be in the aqueous layer or the ether layer, and it
could be on the top or the bottom, depending on the particular reaction that
occur.

In this experiment,we have to separate a prepared mixture of benzoic acid

and a neutral compound (triphenylmethane or 1,2,4,5-tetrachlorobenzene) by
the technique of extraction. The compounds will be extracted on the basis of
the solubility properties of the acids, bases, and their salts. The given unknown
sample will be dissolved with ether. The benzoic acid will be extracted by
adding sodium hydroxide to the dichloromethane solution and using the
process of separation. The benzoic acid will then be isolated using aqueous
hydrochloric acid to turn the solution acidic which will make the benzoic acid
precipitate. The precipitate will be collected using Buchner funnel then put into
oven and will then be weighed and measured for its melting point. Anhydrous
sodium sulfate will be added to the left over ether solution. The mixture will
react and then be filtered, and the solid residue of unknown will be weighed.
Procedure

Extraction

0.24 g of unknown sample and 0.12 g benzoic acid was weight and placed in a
test tube.10 ml of ether was added to the mixture and was shakes to dissolve
the mixture.The solution then transferred to separatory funnel and 5ml of 1 M
NaOH was added, with the cap tight, the layers was mixed by swirling and
shaking for 30 minutes. Pressure was vent by titling the funnel and opening the
stop cork.It was shakes again after closed the stop cork. The mixture was
leaved to standto allow the layers to separate. The aqueous layer was drain into
Erlenmeyer flask and was labeled as first extraction NaOH.5 ml of the 1 M
NaOH solution was added to the ether layer in the funnel and the step I-IV was
repeated and labeled as second extraction NaOH.

Filtration

The flask was taken to the hood and by using glass rod slowly stirring when 6
M HCl was added into each Erlenmeyer flask until the solution was acidic by
using blue litmus paper.The flask then was taken to cool in an ice bath for
about 15 minutes or until thoroughly chilled.The solid benzoic acid was
collected using Buchner funnel and filter flask.2-3 ml water was used to wash
and allowing the suction to continue for five minutes to get solid as dry as
possible.It was scratched gently into watch glass and was put into oven for
complete dryness.The solid was weight and obtain melting point.

Remove NaOH

5 ml or saturated solution of sodium chloride was added to the ether layer in

separatory funnel to remove any trace of NaOH solution.The layer was
separated like before by cap, mixed and vent.The ether layer was transferred
into an Erlenmeyer flask and 1 g of anhydrous sodium sulfate was added to
remove the moisture (water) it contains.The stop cork was closed and swirled
and was leaved to stand for 10 minutes While the ether layer was drying, a
small beaker or Erlenmeyer flask was weight.The dried ether layer was
transferred using Pasteur filter pipette into a beaker. The beaker then brought to
steam bath in the fume hood to evaporate the ether.After evaporated, the beaker
was cool at room temperature and was reweighting to determine the yield of
the unknown sample.The melting point was obtained and compared to the two
chemicals given.
Result and Observation

Actual weight of benzoic acid : 0.1241g

Weight of benzoic acid recovered : 0.0215g
Obseved melting point of benzoic acid (optional) : 124℃
Actual weight of unknown sample : 0.2445g
Weight of unknown sample recovered : 0.1237g
Percent recovery of unknown sample : 50.59%

Observed melting point of unknown sample : 165℃

Literature melting point of triphenylmethanol - 163℃
Literature melting point of or 1,2,4,5-tetrachlorobenzene - 140℃

The identity of your unknown sample : triphenylmethanol

Calculations

Percent benzoic acid recovered = Recovered weight of benzoic acid X 100％

Actual weight of benzoic acid
= 0.0215g X 100％
0.1241g
=17.32％

Percent unknown sample recovered = Recovered weight of unknown sample X 100％

Actual weight of unknown sample
= 0.1237g X 100％
0.2445g
= 50.59％
Discussion

From the result,melting point of unknown sample is 165℃ which was the
nearest to value of melting point of triphenylmethanol which is 163℃. We get
value of meting point higher than the literature melting point of
triphenylmethanol maybe because the melting point apparatus was still hot
when we used.Therefore,it does affect our value of melting point. The percent
recovery of benzoic acid and unknown sample (triphenylmethanol) is not 100%
which is 17.32% and 50.59% respectively. This is cause by the process of
extraction and filtration which the solution does not fully extract by NaOH.The
process of recrystallizing is also incomplete which precipitate can not fully
formed. Next, the drying agent which is anhydrous sodium sulfate bottle was
not fully absorbed the water contains as the bottle was leave to open which
cause ineffectiveness of drying agent.

Conclusion

The process of extraction and vacuum filtration technique should be doing

perfectly and carefully to obtain a better result. This is because it will affect the
percent recovery. We obtained 17.32% of recovered of benzoic acid and
50.59% of recovered of unknown sample (triphenylmethanol). We also has
identified the unknown sample by comparing the value of melting point we
obtained with the given literature of melting point and the unknown solution is
triphenylmethanol.

References

1. CAP.A (2007,OCT 17) Acid/Base Extraction Of A Benzoic Acid, 4-

Nitroaniline,and Naphtalene Mixture Retrieved from
https://adamcap.com/schoolwork/1494/

2. (2018,MARCH 6) Lab 5 Base Extraction of Benzoic Acid from Acetanilide

Retrieved from https://www.studocu.com/en/document/university-of-illinois-
chicago/organic-chemistry-i/mandatory-assignments/lab-5-base-extraction-of-
benzoic-acid-from-acetanilide/1690759/view
3. Nichols.L (2018,MARCH 14) Acid-Base Extraction Retrieved from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book
%3A_Organic_Chemistry_Lab_Techniques_(Nichols)/4%3A_Extraction/4.7%
3A_Acid-Base_Extraction

Question

1. List 4 water-immiscible liquids other than ether that could be used to

extract organic compounds from aqueous solution.
i. Methylene Chloride (dichloromethane)
ii. Chloroform(trichloromethane)
iii. Carbon tetrachloride (tetrachloro-methane)
iv. Cyclohexane

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

chloride open?
The air contain of water, when open the bottle of anhydrous, it expose the
anhydrous to absorb the water molecules in the air, this will affect the
anhydrous effectiveness during experiment.

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 so easily extracted into H2O?

This is because the stronger OH-, removes a hydrogen H+ to form a salt, the
polar salt is soluble in aueous solution, both OH- and benzoate are bases, the
stronger bases takes H+ from the weaker base.

4. Why does benzoic acid precipitate out when the aqueous layer is acidified
with HCl?
This is because the benzoic ion is stronger than Cl-, so each one takes H+
from HCl,the acid forms are not water soluble, so they precipitate out from
solution.