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Experiment No.

9
SYNTHESIS OF ASPIRIN
I. Objectives
At the end oI this activity, we should be able to:
1. %o synthesize a common organic product called acetylsalicylic acid (aspirin).
2. %o become Iamiliar with the optimum conditions needed Ior successIul yield.

II. Materials
Heating setup Funnel Ice
Vial (1) Filter paper Stirring rod
Beaker (1) Syringe (2) Crucible thong

Chemicals

SALICYLIC ACID (C7H6O3(s))














ACE%IC ANHYDRIDE (C4H6O3(s))

PHYSICAL S%A%E Clear liquid, Strong acetic odor
MEL%ING POIN% - 73C
BOILING POIN% 140C
SPECIFIC
GRAVI%Y
1.082
CLASSIFIAC%ION CARBOXYLIC ACID
PHYSICAL S%A%E white to oII-white crystalline powder
MEL%ING POIN% 159 C
BOILING POIN% 211 C
SPECIFIC
GRAVI%Y
1.44
SOLUBILI%Y IN
WA%ER
Slight
SOLVEN%
SOLUBILI%Y
soluble in alcohol, ether, boiling water, sparingly
soluble in chloroIorm
AU%OIGNI%ION 540 C
pH 2.4
VAPOR DENSI%Y 4.8
NFPA RA%INGS Health: 0 Flammability: 1 Reactivity: 0
REFRAC%IVE
INDEX

FLASH POIN%
S%ABILI%Y Stable under ordinary conditions. Light sensitive.
SOLUBILI%Y IN
WA%ER
Slowly soluble (Decomposes)
pH
VAPOR DENSI%Y 3.52
AU%OIGNI%ION
NFPA RA%INGS Health: 3; Flammability: 2; Reactivity: 1
REFRAC%IVE
INDEX

FLASH POIN%
S%ABILI%Y Flammable gas

SULFURIC ACID (H2SO4(conc.))

PHYSICAL S%A%E Colorless (pure) to dark brown, oily, dense liquid with
acrid odor.
MEL%ING POIN% 3 C (100), -32 C (93), -38 C (78), -64 C (65)
BOILING POIN% ca. 290C (decomposes at 340 C)
SPECIFIC
GRAVI%Y
1.84
SOLUBILI%Y IN
WA%ER
Miscible, liberates much heat
pH 1 N solution (ca. 5 w/w) 0.3; 0.1 N solution (ca.
0.5 w/w) 1.2; 0.01 N solution (ca. 0.05 w/w)
2.1
VAPOR DENSI%Y 3.4
REFRAC%IVE
INDEX

NFPA RA%INGS Health: 3 Flammability: 0 Reactivity: 2 Other: Water
reactive
AU%OIGNI%ION
FLASH POIN%
S%ABILI%Y Stable under ordinary conditions


WA%ER (H2O)
Molecular
Iormula
H
2
O
Molar mass 18.01528(33) g/mol
Appearance white solid or almost colorless, transparent, with a slight hint
oI blue, crystalline solid or liquid
Density 1000 kg/m
3
, liquid (4 C) (62.4 lb/cu. It)
917 kg/m
3
, solid










III. Procedure






















Melting point
0 C, 32 F(273.15 K)
Boiling point
99.98 C, 211.97 F (373.13 K)
Acidity (p
a
) 15.74
~3536
Basicity (p
b
) 15.74
ReIractive
index (3
D
)
1.3330
Viscosity 0.001 Pas at 20 C
Prepare a vial
Put 1.2 g salicylic acid in the
vial
Add 0.6 ml acetic anhydride

Add 6 drops oI sulIuric acid
Heat the mixture. Swirl it Ior
5 minutes
Cool down. Add 5 ml oI
cold water
Place it in an ice bath
Filter the crystals

Salicylic acid

Anhydride

Sulphuric acid

Cold water
Leave it in a cool dry place
IV. Data and Results
Salicylic acid acetic anhydride Sulphuric acid they mixed up but not completely
AIter 5 minutes oI heating the solution became very cloudy
-spikes are sparkling iI you look closely
AIter adding water and aIter the ice bath spikes became more visible and longer
AIter Iiltration spikes are very visible and clear

V. Discussions or Questions
Q1. Draw representations oI the molecular structure oI salicylic acid, acetic anhydride and
aspirin.
O salicylic acid



O acetic anhydride


O aspirin


Q2. Write out a balanced chemical equation Ior the reaction oI salicylic acid with acetic
anhydride.
O C7H6O3 C4H6O3 C9H8O4 C2H4O2
2-hydroxybenzoic acid ethanoic anhydride (aspirin) ethanoic acid
Q3. Explain the use oI H2SO4 (conc.) in the experiment.
O %he use oI H2SO4 (conc.) in the experiment will act as an acid catalyst and a dehydrant.
It is also hygroscopic and absorbs water. (Water is released in the synthesis oI aspirin).
Q4. Acetic anhydride is used in excess in this procedure. %his excess can react with the
carboxylic acid group in the aspirin product. Which step in the procedure guards against this?
Explain.
O %he step wherein water is added. %his procedure will guard the excess product to react
with carboxylic because acetic anhydride is soluble in water. So, acetic anhydride will be
dissolve and react with water instead oI the carboxylic acid group.
Q5. What is the purpose oI washing the crystals?
O %he purpose oI washing the crystals is to wash the impurities oI the crystals.

Q6. II 1 microspatula oI salicylic acid has a mass oI approximately 0.2 g, calculate the mass oI
aspirin that should be Iormed.
O %he calculated mass oI aspirin is 1.2 g.

Q7. Assuming you obtained 1 g oI aspirin product, calculate the percentage yield Iormed.
O yield Iormed is 0.0083 .

Q8. One way to prepare an ester is by the reaction oI an alcohol with an acid anhydride (as in
this experiment). However, esters also may be prepared by the reaction between an alcohol and a
carboxylic acid or an alcohol and an acid chloride. Predict the products oI the Iollowing reaction:


CH3COOCH2CH3 HCl




VI. Conclusion

We thereIore conclude that at the end oI this activity we have able to synthesize aspirin
which is the spiky crystals seen aIter the Iiltration process. %he aspirin we have able to
synthesize was white and sparking crystals. %o be able to have the needed yield, the process
should be properly Iollowed and the given measurement should be strictly Iollowed. %he
addition oI water is very important in the process because without this the whole thing will be
destroyed because your excess which is the acetic anhydride will react with other carboxylic
groups, the water will stop this by reacting with the excess instead because acetic anhydride is
soluble to water. Not only addition oI water is important in the process but also the heating and
the ice bath where in Iact all oI the steps and process are important because without them the
synthesize aspirin that we have made will not be successIul.
%he aspirin that we have is also called acetylsalicylic acid. Excess is the acetic acid.

Uses oI aspirin:
Over-the-counter pain relieI, especially Ior headaches, reduction oI swelling and
inIlammation in arthritis and injuries, anti-coagulant given to suIIerers oI heart attack, mini-
stroke and unstable angina, can reduce severity oI heart attack iI taken at Iirst symptoms,
recovery aIter cardiovascular surgery (e.g bypass operation), treatment oI rheumatoid arthritis,
osteoarthritis and other rheumatoid diseases.

%here are also side eIIects oI aspirin:
%he use oI aspirin in children and teenagers with a Iever, especially aIter a viral inIection,
has been associated with the development oI a potentially Iatal condition called Reye Syndrome.
For that reason, it is recommended to NEVER GIVE ASPIRIN %O ANYONE UNDER %HE
AGE OF 16 or to anyone under 20 who has a Iever.