ORGANIC CHEMISTRY (UDEC1164)

BACHELOR OF SCIENCE (HONS) BIOCHEMISTRY

YEAR 1 SEMESTER 1
SESSION: JANUARY 2015
DATE: 11 FEBRUARY 2015
LECTURER: Dr Mohammod Aminuzzaman
EXPERIMENT NO: 2
TITLE: EXTRACTION WITH ACID AND ALKALINE

STUDENTS NAME:

ONG WEI CHING

STUDENTS ID:

1400749

LAB PARTNERS:

INTRODUCTION:

1. YEAP YEE HUNG

2. WONG SHAO JUN

Extraction is a reaction which can separate the dissolving compound or compounds

either from a solid into a solvent or solution into another solvent. The one important
point for extraction is two solvent mixture must insoluble with each other. This mean
that one solvent can be organic compound or non-polar while the other solvent can be
aqueous solution or polar. But, there are also have so exception which the solvent is
able to dissolve in both organic and aqueous solvent. Since the two solutions are not
soluble so two layer will form clearly. Addition of distilled water can help to
determine which solution is aqueous or organic. The increase of volume will be the
aqueous solution. Other reason why two layer will formed because the density of two
solution are different. Usually organic solvent will be used in extraction because
organic solvent has high volatility. It can be removed by evaporation easily and
crystal will form.
Phenolic compounds undergo similar salt formation with sodium hydroxide solution.
So, sodium hydroxide solution can be used to extract a carboxylic acid or phenolic
compound from its solution in an organic solvent. Hence, sodium hydroxide solution
can be used to extract a carboxylic acid or phenolic compound from its solution in an
organic solvent.
The acid-base extraction can used to separate the mixture of carboxylic acid and
neutral compound. The compound separated out will allow to evaporate or purified
into crystal formed and finally the melting point of the compound can be determined.
Not necessary sodium hydroxide must be used in extraction but solution which
consider as strong base can also be used because they have similar properties. The
HCl will convert into their ionic form when strong base is added with the formation of
precipitate.

OBJECTIVES:
To perform extraction by using acid and alkaline.
To recover benzoic acid and p-dichlorobenzene from its mixture using acid-alkaline
extraction method.

MATERIALS:
Benzoic acid, p-dichlorobenzene, ether, 10% NaOH, concentrated HCl, litmus paper,
distilled water, anhydrous CaCl2, boiling chip
APPARATUS:
Separatory funnel (250 ml), Buchner funnel, electronic balance, conical flask, beaker,
hot plate, watch glass
PROCEDURE:

1. 40 ml of ether solution was poured into the small separatory funnel which
contain 1 gram of benzoic acid and 1 gram of p-dichlorobenzene.
2. 20 ml of freshly prepared 10 % NaOH solution was added into the small
separatory funnel.
3. The separatory funnel was shaken well and surplus pressure was released after
the funnel was closed by the stopper.
4. The separatory funnel was allowed to stand.
5. The stopper has been removed and the lower aqueous layer was run into a
conical flask.
6. The residue in the funnel was shaken with another portion of 10 % NaOH
solution.
7. The lower water layer was run off into the same conical flask.
8. Concentrated HCl wad added wisely into the solution into the conical flask
until the mixture become acidic to litmus paper and no further precipitation
occurred.
9. The ether solution was washed by 30 ml of distilled water.
10. The lower layer was run off and discarded.
11. A few granules of anhydrous CaCl2 was added into the ether solution and the
mixture was shaken occasionally until no turbidity remains which is a clear
solution formed.
12. The ether solution was decanted into a clean dry small conical flask.
13. Some boiling chip was added into the ether solution and the solution was
heated until the ether remain approximately 15-20 ml.
14. The ether solution was decanted into a tarred watch glass and the rest of the
ether was set aside to allow it to evaporate, preferably in the fume hood.
15. The precipitated benzoic acid was filtered using a buchner funnel and a flask.
16. The precipitate was washed by 5 ml portion of cold distilled water.
17. A current of air was drawn through the product for about 5 minutes to remove
as much water as possible.
18. The crystal was pressed in a folded filter paper to ensure crystal completely
dry.
19. The weight and melting point of benzoic acid was determined.
20. The p-dichlorobenzene was weight and melting point has been determined as
all the ether has evaporated.

RESULTS:
Weight before separation
Mass of benzoic acid used = 1.0287 g
Mass of p-dichlorobenzene used = 1.0788 g

Weight after separation

Mass of filter paper + benzoic acid crystals = 2.8836 g

Mass of filter paper = 0.6526 g
Mass of benzoic acid crystal = 2.231 g
Theoretical melting point of benzoic acid crystal = 120 C
Experimental melting point of benzoic acid crystal = 112 C
Mass of watch glass + p-dichlorobenzene crystals = 39.6576 g
Mass of watch glass = 37.2724 g
Mass of o-dichlorobenzene crystals = 2.3852 g
Theoretical melting point of p-dichlorobenzene crystals = 53 C
Experimental melting point of p-dichlorobenzene crystals = 55 C

DISCUSSION:
In the experiment, benzoic acid and p-dichlorobenzene are in powder form. Both of
them have to dissolve in the organic solvent which is ether. At this time, both of them
act as uncharged molecules and non-polar. After the addition of sodium hydroxide
(NaOH), it will react with the benzoic acid only. Since the presence of NaOH which is
proton acceptor while benzoic acid will become proton donator. Benzoic acid
(C6H5COOH) will become (C6H5COO) which is negatively charged and polar.
Benzoate ions cannot soluble in organic solvent but can soluble in water so addition
of distilled water will clearly separate the solution into two layers. Upper layer is
organic layer ether react with p-dichlorobenzene while lower layer is aqueous layer
NaOH react with benzoic acid. Two layers formed because of ether do not have
reaction with NaOH while density of both solution also different.

This show that two layers of

solution were formed.

In natural, the uncharged and non-polar organic molecules are able to dissolve in
organic solvent but not water. However, charged and polar molecules are able to
dissolve in water but not organic solvent. The properties of the organic and aqueous

molecules are totally different so the method extraction usually apply on the two
solution which have different properties.
According to the extraction method, separation of benzoic acid and pdichlorobenzene should be done first. The benzoate ions in NaOH solution is more
dense which located at lower layer, it will be run into the conical flask. The second
addition of NaOH is to make sure all the benzoic acid completely reacted. After all of
the lower layer solution run into conical flask, solution remain in separatory funnel
was p-dichlorobenzene in ether. Then, distilled water was added into the separatory
funnel to ensure that no more polar molecule in the organic layer. The lower layer
which is distilled water will be discarded. Few granules of calcium chloride was
added into the ether solution which acts as drying agent to ensure that no more water
in solvent.
Next, the ether solution was discarded into a small beaker. Few number of boiling
chips was added into beaker then beaker is heated on a hot plate to evaporate the
ether. Since ether has high volatility, so after all ether has evaporated only pdichlorobenzene will left inside the beaker. The addition of boiling chips will prevent
boiling over when the boiling chips were heated. This is because inside boiling chip
have a lot of pores which provide spaces to allow bubbles of solvent to be formed. If
boiling over occurred then the product be lost through air and the results will not be
accurate. When the solution left almost 15-20 ml, the beaker was removed from the
hot plate then ether solution was decanted into a watch glass and allowed it to
evaporate. This action prefer done in the fume hood. After the solution evaporate,
white colour crystal which is p-dichlorobenzene will formed on the watch glass.

At the same time, hydrochloric acid (HCl) was added into the conical flask which
contain the benzoate ions. HCl was added until no more white precipitate formed.
Reaction occurred between hydrochloric acid and sodium benzoate is neutralisation.
The formation of white precipitate is benzoic acid while the formation of side product
are sodium chloride and water. The white precipitate was filtered by using a Buchner
funnel and a flask. The precipitates were washed with 5 ml of cold distilled water.
Water was drawn by a current of air for 5 minutes to remove as much water as
possible. The white crystals were formed and dried it by using few piece of filter
paper.
This is the white crystal
which is benzoic acid.

According to the by Le Chateliers principle, addition of hydrochloric acid into the

aqueous solution was able to force the reaction from right to left.
C6H5COOH + NaOH

C6H5COONa+ + H2O

Amount of hydrochloric acid increase caused the amount of hydroxide ions decrease.
To balance the equation, the reaction will automatic shifted from right to left from
benzoate ions to benzoic acid. This reaction convert the charged ions to uncharged
molecule which is not soluble in water so the white precipitate can formed.
For extraction with acid and alkaline, both acid and alkaline must have large
different solubility between charged and uncharged formed of ions. The theory used
in the extraction is the salt which can form ions when soluble in water and become
uncharged molecules when insoluble in water. For example the hydrochloric acid
added into a base and organic acid will convert the acid to uncharged molecule while
the base will be protonated. Addition of acid or base must be correct, if base added
into a base and organic acid solution then the base will remain uncharged and acid
will be protonated.
In this experiment, amount of the theoretical yield usually will more than
experimental yield. But the results of the experiment is accidentally different with
expectation. The inaccurate results may cause by few factors. First is the product
formed was not enough completely dry or may be the filter paper still wet which
cause the weight of the experimental product higher than theoretical product. Next, it
may cause by incomplete reaction and the product was contaminated with other
reagent which has a higher molar mass. Since there are some different between
theoretical melting point and the experimental melting point. This may cause by the
impurities of the product mixed up with other reactant which disturb the arrangement
of the crystal. The energy needed to melt the crystal formed product may be higher or
lower a bit. The mechanism to determine the melting of an element is digital melting
point apparatus.
There are some precautions steps should be taken to avoid fire or injured people
inside the lab. Gloves should be wore and be careful when concentrated hydrochloric
acid was added. The ether is highly flammable so never getting near to the flame. The
position of hand to hold the separatory funnel must be correct to prevent broken of
apparatus.
CALCULATION:
Percent Recovery =

weight of compound recovered

100
weight of compound you started with

Percent Recovery of benzoic acid=

2.231
100
1.0287
=216%

Percent Recovery of pdichlorobenzene=

2.3852
100
1.0788
=221%

Relative Accuracy of Melting Point=

melting point of compound recovery

100
melting point of pure compound

Percent Accuracy of Mel ting Point of Benzoic Acid=

112
100
120
=93.33%

Percent Accuracy of Melting Point of pdichlorobenzene=

55
100
53
=103.77%

CONCLUSION:
Extraction method can used to separate the mixture of organic compound which have
different properties. The extraction experiment must done with very careful so that the
product would not contain too much impurities product. The percentage of benzoic
acid and p-dichlorobenzene recovery is almost 200%. The melting point recovery of
benzoic acid is 93.99% while p-dichlorobenzene is 103.77%.

REFRENCES:
1

T.W.GRAHAM SOLOMON and CRAIG B. FRYHLE, 2012. Organic

Chemistry. 10th ed. United States: John Wiley & Sons, Inc.
2
UK Essays. November 2013. Extraction with Acid and Alkaline Biology
Essay.

[online].

Available

from:

http://www.ukessays.com/essays/biology/extraction-extraction-with-acid-andalkaline-biology-essay.php?cref=1 [Accessed 8 February 2015].

3
Chorco, 2008. Which factors determine the percentage yield in a laboratory
preparation.[online].

Available

[Accessed 8 February 2015].

from:

http://www.ibchem.com/faq/?p=97

UDEC 1164 Organic Chemistry laboratory manual. Experiment 2: Extraction

With Acid and Alkaline. University Tunku Abdul Rahman, Perak.