Visayas State University

Department of Pure and Applied Chemistry

Baybay, City, Leyte

Name: Paciano S. Narita Jr. Date Conducted: March 16, 2018

Score: Date Submitted: March 26, 2018

Experiment No.7
ALDEHYDES AND KETONES

I. Abstract
The main purpose of this experiment was to determine the reactions of Aldehydes and
Ketones. Aldehydes and Ketones are organic compounds consisting of the carbonyl functional
group. Aldehydes contain their carbonyl group at the end of the carbon chain and are susceptible
to oxidation while Ketones contain theirs in the middle of the carbon chain and are resistant to
oxidation. We’ve conducted certain tests in which aldehydes and ketones show positive results in
some reagents and solutions. First test was reaction with 2,4-dinitrophenylhydrazine. In this test
acetone formed a slimy, yellowish solution with a precipitate and the benzaldehyde formed a
yellow suspension with precipitate while the standard formed only slimy, light yellow solution.
The second test was the Tollen’s Test, in this test, formalin and benzaldehyde formed a positive
result which was the formation of silver mirror. The acetone remained the same. Third was the
Schiff’s test, formalin and benzaldehyde turned to dark violet/purple when added with the
Schiff’s reagent. The acetone remained light pink. The fourth test was the Benedict’s test, the
Benedict’s reagent was immiscible in formalin and the solution is blue while the one with
benzaldehyde formed a brick red precipitate at the middle of the solution and when heated the
blue solution disappeared. Fifth was the Iodoform Test, in the test tube with acetone 10 drops of
KI it turned into yellow while the ethanol took 4 drops of KI before it turned yellow. And lastly,
the last test was the Effect of Acid Concentration on Rate Addition of 2,4-
dinitrophenylhydrazine, in 0.1 M acetic acid it took 42 seconds before the crystals disappeared,
0.1 M HCl took 13 seconds before the crystals disappeared and lastly the 6 M HCl took 4
seconds before the crystals disappeared. Base on the results I can conclude the aldehydes are
more reactive than acetones.
II. Introduction
Aldehydes and Ketones are organic compounds that consist of the carbonyl functional group,
C=O. The carbonyl group that consists of one alkyl substituent and one hydrogen is the
Aldehyde and those containing two alkyl substituents are called Ketones. These two organic
compounds undergo reactions that are related to the carbonyl group, however, they can be
distinguished due to their “susceptibility to oxidation”.
The carbonyl of an aldehyde is always at the end of the carbon chain whereas the carbonyl of a
Ketone can lie anywhere within the carbon chain. These two organic compounds are found
abundantly in nature. Since the carbonyl group is polar, aldehydes and ketones have a larger
dipole moment. In the carbonyl group, the positive carbon atom will be attacked by nucleophiles.
Addition reactions can be undergone by carbonyl groups. Since Aldehydes have the hydrogen
atom attached to it, it makes them more susceptible to oxidation, which is the loss of electrons.
However, Ketones lack the hydrogen atom in their carbonyl group and are therefore resistant to
oxidation. Small Aldehydes and Ketones are easily dissolved in water but as the chain increases
in length, its solubility decreases. (1)
The aim of this experiment was to identify the reactions of Aldehydes and Ketones and which
functional groups the unknown substances and known chemicals belonged to, using the different
reaction tests.

III. Methodology
In reaction with 2,4-dinitrophenylhydrazine, we placed 1 mL 95% ethanol in 3 separate test
tubes. One test tube was added 2 drops of acetone, the other was with 2 drops of benzaldehyde
and the 3rd test tube was just ethanol. Then we added the dinitrophenylhydrazine hydrochloride
solution in each of the 3 test tubes.
In Tollen’s Test, we placed the Tollen’s reagent in 3 separate test tubes. One test tube was
dropped (1) with formalin, the other was acetone and the last was dropped (1) with
benzaldehyde.
In Schiff’s Test, we placed 5 drops of Schiff’s reagent in 3 test tubes. We added one drop of
formalin, acetone and benzaldehyde in each test tubes separately.
In Benedict ’s test, we added 2 mL of Benedict’s solution in 2 separate test tubes. To one test
tube we added 5 drops of formalin and to the other 5 drops of benzaldehyde.
In Iodoform test, in 2 separate test tubes we placed 1 mL of 10 % NaOH/. To one test tube we
added 4 drops of acetone and the other 4 drops of ethanol. To each, we added iodine in KI
dropwise with shaking until the solution became yellow.
In Effect of Acid Concentration on rate of Addition of 2,4-dinitrophenylhydrazine, we
prepared a solution of 37 mL acetone contained in 250 mL beaker with dissolved 0.3 g of 2,4-
dinitrophenylhydrazine. After it was already prepared, we placed 1 mL of the prepared solution
in each four test tubes. We kept one tube as a standard. To one tube we added a drop if 0.1 M
acetic acid, to the other a drop of 0.1 M HCl and the last added a drop of 6 M HCl. And
recorded the time when the crystals disappeared.

IV. Results and Discussions

Reaction with 2,4-dinitrophenylhydrazine

Reactants Results
 Acetone Slimy, golden yellow (w/ precipitate)
Benzaldehyde Yellow suspension (w/ precipitate)
Standard Slimy, light yellow
2,4-dinitrophenylhydrazine is a red to orange solid. It is a substituted hydrazine and is often
used to qualitatively test for carbonyl groups associated with aldehydes and ketones. The
hydrazine derivatives can also be used as used toward the identity of the original compound. A
positive test is resulted by a yellow, orange or red precipitate (known as
dinitrophenylhydrazone). If the carbonyl compound is aromatic, then the precipitate will be red;
if aliphatic, then the precipitate will be yellow. Furthermore, acetone and benzaldehyde and its
standard consist of dinitrophenylhydrazone.
Tollen’s Test
Reactants Results
Formalin Silver mirror
Acetone Clear solution, remained the same
Benzaldehyde With flakes of silver mirror on milky solution
Tollen’s reagent is the combination of silver nitrate with ammonium hydroxide is the presence
of NaOH solution.
Aldehydes like formalin and benzaldehyde show a positive result with this reagent because the
reaction between them involves the oxidation of the aldehyde to the corresponding carboxylic
acid and the reduction of the silver ions from this reagent to silver element in the form of silver
mirror on the inner side of the test tube.
Schiff’s Test
Reactants Results
Formalin Dark violet/purple
Acetone Light pink
Benzaldehyde Dark violet/purple
Schiff’s reagent is used for testing aldehydes, it consist of a solution of fuchsin dye that has
been decolorized by sulfur dioxide. Aldehydes reacts with Schiff’s test (as shown in the table
above) to produce a color change (magenta-colored addition product). Schiff’s reagent acts as a
nucleophile that adds to the carbonyl group of an aldehyde.
 Iodoform Test

Reactants Results
Acetone Yellow ppt. gone after a short time during heating
Ethyl Alcohol White ppt. (cloudy) yellow color after heating
Any compounds containing the CH3C=O group or the CH3CH(OH) group gives positive
result with the iodoform test. When I2 and NaOH is added to a compound containing one of
these groups, a pale-yellow precipitate of iodoform(triiodomethane) is formed. Primary alcohols
give positive result in this test, ethanol was oxidized to ethanal which is an aldehyde.

Effect of Acid Concentration on Rate of Addition of 2,4-dinitrophenylhydrazine

Reactants Results
0.1 M acetic acid 42 seconds before the crystals disappeared
1.0 M HCl 13 seconds before the crystals disappeared
6 M HCl 6 seconds before the crystals disappeared
0.1 M acetic acid has the slowest rate of effect of acid concentration then followed by 1 M
HCl and the fastest was the 6 M HCl. This just means that the higher the concentration of the
solution the faster the rate of effect of acid concentration.

V. Conclusion

Base on the experiments conducted, most aldehydes have positive results in different tests
and reagents hence aldehydes are more reactive than ketones. And the higher the concentration
of a solution the faster its rate of rection.

F. Recommendation

Just read the methodology carefully so that you won’t have errors in your experiments. If
possible the chemicals should have distinct droppers to avoid contamination of the experiment.

G. References

www.quora.com/revised March 18,2018

www.chemicalforums.com/revised March 18,2018

www.pubs.rsc.org/revised March 18,2018

Questions
1. By giving the reagent and the visible result, differentiate each of the following pairs:

a)

b)

c)

d) 2-pentanone and 3-pentanone

e) 2-pentanol and 3 pentanol

2. Cite an industrial application of the Tollen’s test.