 Aspirin is a derivative of salicylic acid.

It is a white solid that is almost

completely insoluble in water. It is also
the most widely used medicine in the
world.
INTRODUCTION
 Aspirin can be produced in a one-step
chemical process by reacting salicylic
acid with acetic anhydride.
 To explore the chemical
process in the synthesis
of aspirin
OBJECTIVES To calculate the
percentage yield of
aspirin
POST LAB
QUESTIONS
 1. Compare the reaction mechanism involved in the laboratory synthesis of aspirin and methyl salicylate
 Aspirin is synthesized by mixing salicylic acid with acetic anhydride meanwhile methyl salicylate is prepared
by allowing salicylic acid to react with methyl alcohol. Aspirin and Methyl salicylate are both esters of the
same compound (salicylic acid) but they are also quite different in structure.
2. Relate your results in the ferric chloride and starch tests in the purity of
the synthesized aspirin.

Ferric chloride and starch tests were used to determine the purity of the
synthesized aspirin. For ferric chloride test, ferric chloride forms highly
colored complexes with phenolic compounds. Acetylsalicylic acid does not
contain phenol but salicylic acid does.

When ferric chloride is added, the solution turns purple if salicylic acid is
present and the sample is impure. If it does not turn purple, that means the
sample is pure. We have obtained an impure synthesized aspirin since it
turned into a purple solution. On the other hand, for iodine test, which is a
test for the presence of starch, a blue or blue-black color indicates a positive
result. We have obtained a synthesized aspirin that does not contain starch
since the solution didn’t turn into blue or blue-black color. Only the
commercial aspirin gave a positive result
DATA AND
RESULTS
  A. Reaction of Acetic Anhydride and Salicylic Acid
 Weight of watch glass + salicylic acid 47.7g

 Weight of empty watch glass 45.7g

 Weight of salicylic acid 2g

 Volume of acetic anhydride. 5 mL

 Volume of concentrated sulfuric acid. 5 drops

 Weight of filter paper + product. 3.67g

 Weight of dry filter paper.

GROUP 1  Weight of product.
1.55g

1.12g

 Calculate the theoretical yield

 Compute for the percentage yield:

  A. Reaction of Acetic Anhydride and Salicylic Acid
 Weight of watch glass + salicylic acid 45.9g
 Weight of empty watch glass 43.9g
 Weight of salicylic acid 2g
 Volume of acetic anhydride. 5 mL
 Volume of concentrated sulfuric acid. 5 drops
 Weight of filter paper + product. 3.54g
 Weight of dry filter paper. 1.06g
 Weight of product.
GROUP 2  Calculate the theoretical yield
2.48g
2.73g

 Compute for the percentage yield:

 %yield = actual yield/theoretical yield x 100
 = 2.48g/2.73g x 100
 = 90.84%
  A. Reaction of Acetic Anhydride and Salicylic Acid
 Weight of watch glass + salicylic acid 45.8g

 Weight of empty watch glass 43.8g

 Weight of salicylic acid 2g

 Volume of acetic anhydride. 5 mL

 Volume of concentrated sulfuric acid.

 Weight of filter paper + product.
 Weight of dry filter paper.
GROUP 3  Weight of product.
 Calculate the theoretical yield

 Compute for the percentage yield:

  A. Reaction of Acetic Anhydride and Salicylic Acid
 Weight of watch glass + salicylic acid 47.8g

 Weight of empty watch glass 45.8g

 Weight of salicylic acid 2g

 Volume of acetic anhydride. 5 mL

 Volume of concentrated sulfuric acid. 5 drops

 Weight of filter paper + product. 6.7g

GROUP 4  Weight of dry filter paper. 1.6g

 Weight of product. 5.1g

 Calculate the theoretical yield

 Compute for the percentage yield:

  A. Reaction of Acetic Anhydride and Salicylic Acid
 Weight of watch glass + salicylic acid 45.8g
 Weight of empty watch glass 43.8g
 Weight of salicylic acid 2g
 Volume of acetic anhydride. 5 mL
 Volume of concentrated sulfuric acid. 5 drops
 Weight of filter paper + product. 2.9901g
 Weight of dry filter paper. 1.6g

GROUP 5  Weight of product. 1.3901g

 Calculate the theoretical yield 2.6193g C9H8O4

 Compute for the percentage yield:

 %yield = amount of sample obtained/ amount of sample used x 100

 = 1.3901g / 2 x 100
 = 69.505 %
  A. Reaction of Acetic Anhydride and Salicylic Acid
 Weight of watch glass + salicylic acid 44.93g

 Weight of empty watch glass. 42.93g

 Weight of salicylic acid 2g

 Volume of acetic anhydride. 5 mL

 Volume of concentrated sulfuric acid. 5 drops

 Weight of filter paper + product. 3.56g

GROUP 6  Weight of dry filter paper. 1.5g

 Weight of product. 2.06g

 Calculate the theoretical yield

 Compute for the percentage yield:

 B. Ferric Chloride test
Test tube Observations Inference

Salicylic acid Very dark violet Violet

Commercial Dark violet Violet

aspirin

Synthesized Violet Violet

GROUP 1 aspirin

Benzoic acid Cloudy light orange Orange

Benzyl alcohol Cloudy white White

Control Clear orange Orange

 B. Ferric Chloride test
Test tube Observations Inference

Salicylic acid Change to a violet There is a

color presence of
salicylate

Commercial Change to a violet Presence of

aspirin color salicylate

GROUP 2 Synthesized
aspirin
Change to a light
violet color
Presence of
salicylate
Benzoic acid Change to yellowish No presence of
brown, cloudy salicylate
solution

Benzyl alcohol None/ no reaction No presence of

salicylate
Control None/ no reaction No presence of
salicylate
 B. Ferric Chloride Test
Test tube Observations Inference

Salicylic acid Dark purple There is a

presence of
salicylate

Commercial Dark purple Presence of

aspirin salicylate
Synthesized Purple Presence of
aspirin salicylate
GROUP 3 Benzoic acid Light orange No presence of
salicylate

Benzyl alcohol None No presence of

salicylate
Control None No presence of
salicylate
 B. Ferric Chloride test
Test tube Observations Inference

Salicylic acid Dark violet with

solid white powder

Commercial Light violet with

aspirin solid white powder

Synthesized Colorless liquid

GROUP 4 aspirin with jelly substance

Benzoic acid Violet with solid

white large crystals

Benzyl alcohol Colorless liquid

with jelly substance

Control Colorless only

 B. Ferric Chloride test
Test tube Observations Inference
Salicylic acid Violet solution Salicylic acid is
present
Commercial Violet solution with Salicylic acid is
aspirin precipitate present
Synthesized Light violet solution Salicylic acid is
aspirin present
Benzoic acid Light orange solution No presence of
salicylic acid
GROUP 5 Benzyl alcohol Yellow solution with No presence of
oily layer salicylic acid
Control Without ferric No presence of
chloride: colorless salicylic acid

With ferric chloride:

light yellow solution
 B. Ferric Chloride test
Test tube Observations Inference

Salicylic acid Dark violet solution (+) Salicylic acid

is present
Commercial Violet solution (+) Salicylic acid
aspirin is present

Synthesized Purple solution (+) Salicylic acid

GROUP 6 aspirin is present
Benzoic acid Light orange solution (-) No salicylic
acid is present
Benzyl alcohol Oily solution (-) No salicylic
acid is present

Control No reaction (-) No salicylic

acid is present
 C. Starch test

Test tube Group 1 Group 2 Group 3 Group 4 Group 5 Group 6

Commercial Blue- black Change to Dark yellow Black Black solution (+) Blue-
aspirin with starch black color with black presence of black
precipitate starch solution

Synthesized aspirin Clear yellow Change to Yellow Yellow with Yellow No reaction
yellow color white powder solution

Control Clear yellow Change to Gold Yellow Yellow No reaction

yellow color No presence solution
of starch
  D. Preparation of Methyl Salicylate

Group 1 Group 2 Group 3 Group 4 Group 5 Group 6

Methyl Minty odor Mint Minty Minty Minty odor Mint

Salicylate aroma smell aroma aroma
  Methyl Salicylate is a naturally occurring chemical that is
obtained from winter green oil that can be used to
synthesize Salicylic Acid. Methyl Salicylate is a phenol with
a acetyl group in the ortho position. This carbonyl group
can undergo typical carbonyl addition-elimination
reactions
 An addition elimination reaction occurs at the carbonyl
carbon where a nucleophile attacks the highly
CONCLUSION electrophilic carbonyl carbon. The carbonyl carbon is
more electrophilic than the other carbons because the
double bonded oxygen withdraws a great amount of the
electron density making the carbon highly electropositive.
After the nucleophile attacks the carbon, a tetrahedral
intermediate with 4 substituents are coming off of the
central carbon, one being an oxygen anion, is formed.
Then the substituent that is the best leaving group leaves,
and the carbonyl group is reformed.