Name: Sanglad, Chariezza Lei J.

Date Performed: July 7, 2017

Group No:5 Date Submitted: July 14, 2017

Experiment no:4

QUALITATIVE TESTS FOR THE FUNCTIONAL GROUPS IN ASPIRIN

Objectives:
1. To be able to test qualitatively for the functional groups in aspirin.
2. To be able to determine the functional groups present in aspirin.

Procedure:
Test for Alcohol
Chromic Acid Test
Test tube
Aspirin
+ 5% K2Cr2O4 + 5%H2SO4
Boiling water bath
Record time for sol’n to change
Color
Note color change and odor
Lucas Test
Test tube
Aspirin + lucas reagent
Shake, let stand
Record time for formation of insoluble layer
Test for Phenol
Ferric Chloride Test
Test tube
Aspirin +1% FeCl2
Note color
Test for Aldehyde
Tollen’s Test
Test tube
Aspirin + tollen’s reagent
Shake
Observe color
Test for Ketone
Iodoform Test
Test tube
Aspirin
+ iodine in KI sol’n
+ 10% NaOH until color of iodine discharged
Warm bath
Note odor of vapors and color of precipitate
Test for the Carbonyl Group

2,4-Dinitrophenyhydrazine Test

test tube

aspirin

+ 2,4-dinitrophenyhydrazine reagent

Shake

Note time
Test for Carboxylic acid

Esterification

Test tube

Aspirin

+ n-propyl alcohol + H2SO4

Note time required

Test for Ester

Hydroxamic Test

Preliminary test

Test tube

Aspirin

+ HCl + 5% FeCl3

Note color produced

Final test

Test tube

Aspirin

+ ethyl acetate w/ 0.5 hydroxylamine hydrochloride in 95% alcohol

+ 6N NaOH

Δ boiling H2O bath

Cool slightly

+ 1N HCl + 5% FeCl3

Note color produced

Test for Amide

Hydrolysis test

Test tube

Aspirin

+ 10% NaOH

Δ boiling H2O

Observe gas evolve

Test gas w/ moist red litmus paper

Test for Amine

Ninhydrin test

Test tube

Aspirin

+ 10% NaOH

Δ boiling H2O

Note color produced

Data and Results
Table 1. Observation for Qualitative Test for Functional Group in Aspirin.
Test Test Treatment Observations Inference
Sam-
ple

Test for Chromic Acid Test + 5% K2Cr2O4 + No green Absence of

Alcohol 5%H2SO4, Δ Boiling color of Alcohol
water bath solution
A
LucasTest + lucas reagent No insoluble Absence of
layer formed Alcohol
S
Test for Ferric Chloride Test +1% FeCl2 Purple color Presence of
Phenol solution Phenol
P
Test for Tollen’s Test + tollen’s reagent No silver Absence of
Aldehyde mirror Aldeyde
I
Test for Iodoform Test + iodine in KI sol’n,+ No yellow Absence of
Ketone 10% precipitate Ketone
R NaOH,WarmBath

Test for 2, 4 + 2,4- No orange Absence

I Carbonyl Dinitrophenylhydrazine dinitrophenyhydrazine precipitate,No ofCarbonyl
Group Test reagent medical smell Group
N
Test for Esterification + n-propyl alcohol + Formation of Presence of
Carboxylic H2SO4 Pleasant Odor Carboxylic
Test Group

Test for Hydroxamic Test + HCl + 5% FeCl3 Yellow Color Presence of

Ester (Preliminay) solution Ester

Hydroxamic Test + ethyl acetate w/ 0.5 Purple Color Presence of

(Final) hydroxylamine solution Ester
hydrochloride in 95%
alcohol,+ 6N NaOH, Δ
boiling H2O bath,
Cool,+ 1N HCl + 5%
FeCl3

Test for Hydrolysis Test + 10% NaOH, Δ Red litmus Presence of

Amide boiling H2O paper turned Amide
blue

Test for Ninhydrin Test + 10% NaOH, Δ No purple Absence of

Amine boiling H2O color solution Amine
Discussion

In the test for alcohol using chromic acid test, the disappearance of the red-orange color of
chromic acid and the formation of a blue-green color of the Cr (III) ion indicates a positive test.
Note that if the unknown is not soluble in water, two layers may be present. A blue-green color in
either layer indicates a positive test. In the experiment, no green color was observed. Hence, a
negative result for alcohol.

Lucas reagent was used in test for alcohol. A positive test for primary or secondary alcohols
consists in the production of an opaque suspension with a green to blue color. Tertiary alcohols
give no visible reaction within 2 seconds, the solution remaining orange in color. Disregard any
changes after 15 seconds. Appearance of a cloudy second layer or emulsion; 3o alcohols:
immediate to 2-3 minutes ;2o alcohols: 5 -10 minutes; 1o alcohols: no reaction. In the experiment,
no insoluble layer was formed. So, a negative result for alcohol.

In test for phenol using ferric chloride, compounds with a phenol group will form a blue,
violet, purple, green, or red-brown color upon addition of aqueous ferric chloride.

In the experiment, a purple color of solution was observed. Therefore, a presence of phenol is
concluded.

In the test for aldehyde using Tollen’s test, also known as silver-mirror test, is a qualitative
laboratory test used to distinguish between an aldehyde and a ketone. It exploits the fact that
aldehydes are readily oxidized. Tollens’ test uses a reagent known as Tollens’ reagent, which is a
colorless, basic, aqueous solution containing silver ions coordinated to
ammonia [Ag(NH3)2+][Ag(NH3)2+]. The reaction is accompanied by the reduction of silver ions
in Tollens’ reagent into metallic silver, which, if the test is carried out in a clean glass test tube,
forms a mirror on the test tube. In the experiment, no silver mirror was formed and with this result,
it indicates no aldehyde group is present in aspirin.

In the test for ketone using iodoform test, iodine solution is added to a small amount of
aldehyde or ketone, followed by just enough sodium hydroxide solution to remove the color of the
iodine. If nothing happens in the cold, it may be necessary to warm the mixture very gently. A
positive result is the appearance of a very pale yellow precipitate of triiodomethane (previously
known as iodoform) - CHI3. Apart from its color, this can be recognized by its faintly "medical"
smell. In the experiment, no yellow precipitate was formed. It indicates that no ketone group is
present in aspirin.
 In the test for Carbonyl group using 2,4-dinitrophenyhydrazine test, carbonyl group react
with 2,4-dinitrophenylhydrazine reagent to form orange precipitates. Formation of a precipitate
therefore indicates the presence of an carbonyl group. In the experiment, no orange precipitate was
formed which indicates no carbonyl group is present in aspirin.

For Carboxylic acid using esterification, Esters have a hydrocarbon group of some sort
replacing the hydrogen in the -COOH group of a carboxylic acid. At cases where it is replaced by
an alkyl group, but it could equally well be an aryl group (one based on a benzene ring). Esters
have a hydrocarbon group of some sort replacing the hydrogen in the -COOH group of a carboxylic
acid. We shall just be looking at cases where it is replaced by an alkyl group, but it could equally
well be an aryl group (one based on a benzene ring).

Carboxylic acid reacts with alcohol in presence of conc. sulphuric acid to form ester that is
identified by the presence of a fruity smell. In the experiment, a pleasant odor was smelled which
indicates a presence of Carboxylic acid group.

In test for esters, hydroxamic test was used. This reaction is utilized in a spot test for
carboxylic acids because hydroxamic acids formed give a yellow, red or purple color with ferric
chloride in acid solution (carboxylic acid is converted into its acid chloride). In the experiment, a
yellow color solution and purple color solution was observed in preliminary and final test
respectively. It indicates a presence of ester in aspirin.

Hydrolysis Test was used in the test for amide. Technically, hydrolysis is a reaction with
water. That is exactly what happens when amides are hydrolyzed in the presence of dilute acids
such as dilute hydrochloric acid. The acid acts as a catalyst for the reaction between the amide and
water. If sodium hydroxide solution was added to an unknown organic compound, and it gives off
ammonia on heating (but not immediately in the cold), then it is an amide. The ammonia can be
recognized by smell and because it turns red litmus paper blue. The possible confusion using this
test is with ammonium salts. Ammonium salts also produce ammonia with sodium hydroxide
solution, but in this case there is always enough ammonia produced in the cold for the smell to be
immediately obvious.

In the experiment, the red litmus paper turned blue therefore a presence of amide can be concluded
in the organic compound which is aspirin.
 Ninhydrin test was used in the test for amine. Ninhydrin (2,2-dihydroxyindane-1,3-dione)
is a chemical used to detect ammonia or primary and secondary amines. When reacting with these
free amines, a deep blue or purple color known as Ruhemann's purple is produced. Amines
(including α-amino acids) react with ninhydrin to give a coloured product.It can be used
qualitatively (e.g. for chromatographic visualisation) or quantitatively (e.g. for peptide
sequencing).The α-amino acids typically give a blue-purple product.Proline, a secondary amine,
gives a yellow-orange product. In the experiment, no blue or purple color was observed. With this
result, it indicates that no amine is present in aspirin.
Data and Results
Table1. Observation for the Melting Point of Aspirin.

Trial Sample Treat- Observation Theoretical Percent

(inside ment Temperature reading Average value Error
capillar every 20s interval Melting (melting
y tube) Point point)

1
Aspirin Oil bath 138.67°C 135°C 0.03%
137ᵒC 139ᵒC 140ᵒC
2
Aspirin Oil bath 139°C 135°C 0.03%
138ᵒC 139ᵒC 140ᵒC

Discussion:
Melting point analysis can also provide information about the purity of a sample. A
substance (solid) containing soluble impurities usually melts at a lower temperature than the pure
compound. It can also melt over a wide range of temperatures. This is called the “melting point
depression”. In general, the smaller the range of melting temperatures, the higher the purity of the
sample.

In our experiment, as for the melting point data, the range of the trial 1 sample was 137-
140˚C and the range of the trial 2 sample was 138-140˚C. Comparing the results to the literature
value of 135˚C, both the two trials had a precise value. The percentage yield of the final product
was calculated to be 85.01%. It can be concluded that by recrystallizing the aspirin, though it
decreased the percentage yield, a significantly purer aspirin was produced, as shown by the more
feasible and realistic melting range. Aspirin has a theoretical melting range of 134-136°C. The
percentage error for the first trial was 0.03% and for the second trial was also 0.03%.

Pure aspirin was obtained after filtering out the impurities and excess reagent through filter
paper since the melting point of first and second trials were closed to the theoretical melting point
of aspirin. A method to check a solid compound's purity after re-crystallization is to check its
melting point. Impurities will always lower the melting point of a sample.

Calculations:

Melting Range Percentage Error

As the melting point is a range, the average value of the range will be found before
calculating percentage error.

Average of actual melting range in trial 1 = 138.67°C

Expected melting point = 135°C
Theoretical Value−Actual value
Percentage error = Theoretical Value
x 100%

135−138.67
=/ /x 100%
135
=0.03%

Average of actual melting range in trial 2 = 139°C

Expected melting point = 135°C
Theoretical Value−Actual value
Percentage error = x 100%
Theoretical Value
 135−139
=/ /x 100%
135
=0.03%