ALDEHYDES AND KETONES

RESULTS
Table 1. General Test for Carbonyl Compounds (Aldehydes and Ketones):
Nucleophilic Addition of 2,4-DNPH

Description of Product
(Phenylhydrazone)

Carbonyl
Compound

Test
Response
(+/-)

Chem
Rxn

Formaldehyde
Benzaldehyde
Acetone
Chemical Equations:

1a

1b

1c

+ H 2O

Table 2. General Test for Aldehydes: Oxidation by Tollens Reagent

General Equation:

Carbonyl
Compound
Formaldehyde

Description of Resulting Mixture

Ag mirror was formed; Clear solution

Test
Response
(+/-)

Che
m
Rxn

2a

ALDEHYDES AND KETONES

Benzaldehyde

Formation of emulsion; Dirty white solution

2b

Acetone

No Ag mirror formed; Clear solution

2c

Chemical Equations:
2a

2b
NO REACTION
2c
No reaction

Table 3. General Test for Aliphatic Aldehydes: Oxidation by Fehlings Reagent

General Equation:
Test
Response
(+/-)

Chem
Rxn

Carbonyl
Compound

Description of Resulting Mixture

Formaldehyde

Blue solution Brick red precipitate was

formed

3a

Benzaldehyde

Lighter blue No precipitate formed

3b

Acetone

Dark blue solution No precipitate formed

3c

Chemical Equations:
3a

ALDEHYDES AND KETONES

3b

2C6H6CHO + NaOH C6H6CH2OH +C6H6COONa

3c
No reaction

Table 4. Preservative Action of Formaldehyde

Protein
Sample

Description of Sample

Description of Sample
in Hot Water

Untreated
gelatin sheet

Did not dissolve in water

Gelatin sheet
treated with
H2C=O

Dissolved in water

Solubil
ity in
H2O
(+/-)
+

Table 5. Oxidation by KMnO4

Test
Response
(+/-)

Chem
Rxn

Carbonyl
Compound

Description of Resulting Mixture

Formaldehyde

Pink solution Yellow solution with red

precipitate

5a

Acetone

Pink solution

5b

Chemical Equations:
5a

5C6H6CHO + 2KMnO4 + 6H+ 5C6H6COOH +2Mn2+ + 3H2O + 2K+

ALDEHYDES AND KETONES

5b

CH3COCH3 + KMnO4 No reaction

Table 6. Test for CH3C=O or methyl ketone group in carbonyl compound: Iodoform
Test

Carbonyl
Compound

Description of Resulting Mixture

Test
Response
(+/-)

Chem
Rxn

Formaldehyde

Brown solution White precipitate

6a

Acetone

Clear solution with white precipitate

6b

Chemical Equations:
6a

+ I2 + OH- No reaction
+ I2 + OH- No reaction

6b

DISCUSSION
This experiment is all about performing tests in order to know whether which
of the following compounds are aldehydes and which are ketones.
In the general test for Carbonyl compounds, 2,4-dinitrophenylhydrazine was
used. Aldehydes and ketones react with a number of nitrogen containing compounds
through nucleophilic addition and subsequent loss of water to give products that
havea carbon nitrogen double bond. The color of the hydrazone precipitate formed is
often a guide to the amount f conjugation in the original aldehyde or ketone.
Unconjugated ketones such as cyclohexanone often give a yellow solid, while
conjugated ketones such as acetophenone give orange to red solids. Compounds
which are highly conjugated give red solids. 2,4-dinitrophenylhydrazine already was
orange-red itself; thus the color must be judged with caution. There were three test
tubes prepared, each one for a different test compounds; one for formaldehyde, one
for benzaldehyde and one for acetone. Each of the three test tubes was already

ALDEHYDES AND KETONES

containing mL of 95% ethanol and a drop of each test compound was added to
each of which it is assigned. The test tube with
Second was the Tollens test which is the general test for Aldehydes.
Aldehydes are very easily oxidized to yield carboxylic acid or their salts if the reaction
is done in basic media. Since ketones are not readily oxidized, this test is a useful
method of differentiating between aldehydes and ketones. The solution used in this
test was an ammoniacal silver hydroxide solution which is a very mild oxidizing agent.
When the reaction is positive, a silver mirror sometimes is formed on the test tube
which is resulted from the reduction of the silver ion to metallic silver. Ordinary
ketones do not give a positive result in this test. Again, there were three test tubes
prepared, each for the different test compounds. Each test tube was occupied with
1mL of Tollens solution. A drop of each test compound were added to each assigned
test tube. The test tube with formaldehyde and Tollenssolution reacted positively and
formed a silver mirror, while the test tubes with bezaldehyde and acetone didnt react
positively. There was an emulsion formed in the test tube with benzaldehyde while
the test tube with acetone didnt show any reaction at all.
Third was the general test for Aliphatic Aldehydes or the Fehlings test. There
were two solutions used for this test; the Fehlings A, which was a blue aqueous
solution of copper(II) sulfate, and the Fehlings B, which was a clear and colorless
solution of aqueous potassium sodium tartate and a strong alkali. The formation of
brick-red precipitate of cuprous oxide indicates the positivity and indicates that the
compound is an aldehyde. There were three test tubes prepared, each for each
assigned test compound. Each test tube contains a half mL of the Fehlings A solution
and another half of the Fehlings B. A drop of each solution was added to each test
tube. Then each was warmed in a water bath. Only the test tube with the test
compound formaldehyde reacted positively, with a colored blue solution and brick-red
precipitate. The two other test tubes with benzaldehyde and acetone, respectively,
were also blue in color but didnt produce any precipitate.

Next was the oxidation by KMnO4, Potassium permanganate is a strong

oxidizing agent used to test the presence of an aldehyde or a ketone. If the
compound present is an aldehyde, it will be readily oxidized by the potassium
permanganate into a carboxylic acid due to the presence of the hydrogen
atom bonded to the carbonyl group. If the compound present is a ketone, it is
generally not oxidized by potassium permanganate, unless in extreme
conditions such as the presence of heat. If KMnO 4 is able to oxidize the
ketone, a cleavage mixture of two carboxylic acids would be present in the
solution. The result when 5 drops of 0.0002M KMnO4 to formaldehyde is a pink
solution. It was then acidified by dilute H2SO4, there was a red precipitate. On
the other hand, there was no reaction when acetone is used. Theoretically,
formaldehyde, benzaldehyde and cyclohexanone would positive results, since
they would be oxidized by potassium permanganate to form brown
manganese dioxide. On the other hand, acetone is not expected to produce a
positive result for potassium permanganate.

ALDEHYDES AND KETONES

The test for methyl ketone group or the Iodoform test was the last test
performed. Methyl ketones can be distinguished from other ketones by their reaction
with iodine in a basic solution to yield iodoform (CH 3I) as a yellow colored precipitate.
However, acetaldehyde (CH3CHO) will also form iodoform under the same conditions.
Alcohols of the type described are easily oxidized to methyl ketones under the
conditions of the iodoform reaction. Two test tubes were prepared and occupied with
a solution of formaldehyde and acetone (5 drops of each compound with 2 mL water).
Five drops of I2 solution and a few drops of NaOH were added until the brown solution
was discharged. It was then warmed in water bath. After the water bath, the
formaldehyde solution with I2 and a few drops of NaOH was still brown in color and
produced some white precipitate. However, the acetone solution changed its solution
color from brown to white and like the formaldehyde solution, the acetone solution
produced some white precipitate.
References:

1. http://www.chemguide.co.uk/organicprops/carbonyls/oxidation.html
2. http://www.wikipremed.com/03_organicmechanisms.php?
mch_code=030208_030
3. http://www.chemguide.co.uk/organicprops/carbonyls/addelim.html
4. http://en.wikipedia.org/wiki/Fehling's_solution
Abstract
A qualitative analysis of aldehydes and ketones was conducted in the
experiment. Four test samples, namely acetone, formaldehyde and
benzaldehyde were used in the experiment. Various parameters regarding the
physical properties of aldehydes and ketones were determined using tests
such
as
the
oxidation
with
potassium
permanganate,
2,4dinitrophenylhydrazine test, Tollens test, Fehlings test, iodoform test and
action of formaldehyde on protein substances. The objectives of the
experiment were met since the physical properties of the aldehydes and
ketones were observed using the tests. However, some experimental results
deviated from the theoretical one, such as the non-oxidation of formaldehyde
with potassium permanganate. These unforeseen errors and deviations in the
result of the experiment can be attributed to the impurities that may have
altered the original result. The experiment would be very helpful in
establishing the identity of a certain unknown compound.
Conclusion
The objectives of the experiment were met after the experiment. This is
due to the fact that the physical properties of aldehydes and ketones were
observed using the four test samples. However, some unexpected results
were recorded, such as the non-oxidation of formaldehyde in potassium
permanganate and the negative results of acetone and formaldehyde.
The deviations of the experimental results from the theoretical one may be
attributed to the impurities present in some of the samples. These impurities

ALDEHYDES AND KETONES

present may have hindered any reaction, or produced a new reaction which
may be the reason why the results deviated from the expected one.
In order to avoid the confusion in determining whether the compound is an
aldehyde or a ketone, it is recommended to conduct additional tests that
would better establish the identity of a certain compound
Procedure
A.
a. General Test for Carbonyl Compounds
1. 1 drop of the test compound was added in a test tube containing mL of
95% ethanol.
2. mL of 2,4-DNPH was added next.
3. Shaked and stand for few minutes.
b. Tollens Test
1. 1 mL of Tollens solution was transferred in a clean test tube.
2. 1 drop of test compound was then added.
3. Mixed and warmed in a water bath.
c. Fehlings Test
1. 1 drop of the test compound was added to a test tube containing mL of
Fehlings A and Fehlings B.
2. Mixed and warmed in a water bath.
B.
d. Action of Formaldehyde on Protein Substances
1. 2 mL of formaldehyde was mixed with 2 mL water in a small test tube.
2. Shaked.
3. Strip of gelatin sheet was divided into two.
4. strip of a gelatin sheet was dipped into the solution.
5. The sheet was removed.
6. Solubility was tested.
e. Oxidation by KMnO4
1. mL of formaldehyde was added to a test tube with 5 drops of 0.0002M
KMnO4.
2. Acidified with a few drops of dilute H2SO4.
3. Mixed.
f. Iodoform Test
1. Solutions of formaldehyde and acetone was made.
2. 5 drops of I2 solution was added and then dilute NaOH solution.