Organic Compounds with

Carbonyl Group:

Aldehydes and Ketones

Laboratory Report

CAMPUGAN-CARCUEVA-CARREON-CENIA-CUEVAS-DALANIEL
Outcomes:

To compare chemical reactivity of

aldehydes and ketones
 Apparatus

test tube and test tube rack test tube holder pipette medicine dropper 10 ml graduated cylinder

bunsen burner water bath wire gauze 400 ml beaker

 JULY 2022

Materials

2,4 Tollen’s reagent,

Formaldehyde benzaldehyde acetone Fehling’s reagent
dinitrophenylhydrazine

Schiff’s reagent potasium permanganate diluted sulfuric acid water

10%sodium hydroxide iodine solution
solution solution
 Introduction

An aldehyde is an organic compound:

containing a terminal carbonyl group. This functional group, called an aldehyde group,
consists of a carbon atom bonded to a hydrogen atom with a single covalent bond
and an oxygen atom with a double bond.
chemical formula for an aldehyde functional group is -CH=O, and the
general formula for an aldehyde is R-CH=O.
The aldehyde group is occasionally called the formyl or methanoyl group

A ketone, any of a class of organic compounds

characterized by the presence of a carbonyl group
carbon atom is covalently bonded to an oxygen atom.
the remaining two bonds are to other carbon atoms or hydrocarbon
radicals (R)
Physical properties of formaldehyde,
benzaldehyde and acetone.

Properties Formaldehyde Benzaldehyde Acetone

Color colorless colorless colorless

almond -like
Odor strong odor pungent odor
odor
highly
Flammability flammable flammable
flammable

Volatility volatile volatile volatile

Physical properties of formaldehyde,
benzaldehyde and acetone.

Properties Formaldehyde Benzaldehyde Acetone

Solubility in readily soluble slightly soluble readily soluble

water in water in water in water
Solubility in completely
soluble soluble
alcohol soluble
 2,4 Dinitrophenylhydrazine Test

Procedure
3 to 5 drops of formaldehyde, benzaldehyde, and acetone were placed in three
separate test tubes. Then 3 to 5 drops of 2,4 -dinitrophenylhydrazine were added
in each test tube. Changes were observed and recorded

Results and Analysis

In the first test tube containing formaldehyde, the
solution turned into cloudy orange when 2,4 -
dinitrophenylhydrazine was added. The test tube
with benzaldehyde, it turned into cloudy orange
with small particles at the bottom. For the third
tube with acetone, the solution turned into clear
yellow
 2,4 Dinitrophenylhydrazine Test
Chemical reaction

Discussion
When all the chemicals in the test tubes react with 2,4-dinitrophenylhydrazine,
they produced a positive result. When the 2,4-dinitrophenylhydrazine reagent
was applied, 2 of the compounds (formaldehyde and benzaldehyde) formed
an orange precipitate and 1 compound (eacetone) formed a yellow precipitate.
The presence of C=O bond can be detected by this experiment.
 2,4 Dinitrophenylhydrazine Test

Conclusion

A convenient way of testing aldehydes and

ketones is by testing them with an aqueous
solution of 2,4-dinitrophenylhydrazine (known
as Brady's reagent). A yellow, orange or 2,4-dinitrophenylhidrazine
reddish-orange precipitate of
dinitrophenylhydrazine develops if an aldehyde
or ketone is present.
 Tollen's Test
Procedure
3 to 5 drops of formaldehyde, benzaldehyde and acetone were placed in 3 separate
test tubes. Then 3 to 5 drops of freshly-prepared Tollen’s reagent were added to
each test tube. Shaken and warmed gently in a water bath in 3 minutes. Changes were
observed and recorded BEFORE WARM BATH

Results and Analysis

When the test tube that contains formaldehyde was added with
freshly-prepared Tollen's reagent, the color changed from transparent
to black precipitate. However when it was warmed, the color again
changed into white silver. On the other hand, the test tube with
AFTER WARM BATH
benzaldehyde had silver flakes on the inner surface but eventually
changed into black precipitate when warmed. Unlike formaldehyde and
benzaldehyde, there is no change or reaction that happened when
the test tube with acetone was dropped with Tollen's reagent.
 Tollen's Test
Chemical Reaction

Discussion
Both the formaldehyde and benzaldehyde give a positive test with Tollens
reagent. When an aldehyde is added with tollen's reagent, Ag20 is reduced to
silver which deposits as black precipitate or silver mirror. On the other hand, the
acetone gives a negative test. Acetone is a ketone which is not oxidized by
Tollens’ reagent, so the treatment of a ketone with Tollens’ reagent in a glass
test tube does not result in a silver mirror.
 Tollen's Test

Conclusion
The Tollens' test, commonly known as the silver-mirror test, is a test used for
determining the difference between an aldehyde and a ketone. It takes advantage
of the fact that aldehydes, unlike ketones, are easily oxidized. A positive test
result in Tollen's test can be obtained if there is a formation of black or silver
precipitate. If the sample is not an aldehyde, then it will give a negative result.
 Fehling's Test

Procedure
Three clean test tubes were filled with three to five drops of formaldehyde,
benzaldehyde, and acetone, respectively. Then, in each test tube, we added
1.0 ml of Fehling's A and B solution. Following that, the test tubes were
shaken and placed in a water bath for 3 minutes.

Results and Analysis

As the formaldehyde solution was removed from the

water bath, it precipitated into a brick-red precipitate.
When heated in the water bath, the test tube
containing benzaldehyde and acetone produces no
reaction.
Fehling's Test
Chemical Reaction

Discussion
Only the formaldehyde-containing test tube produced a positive result, forming
a brick-red precipitate. Because benzaldehyde lacks alpha hydrogen,
intermediate enolate formation does not occur. As a result, it does not react to
Fehling's solution. Ketone, on the other hand, does not react with Fehling's
solution unless it is alpha-hydroxy ketone.
Conclusion
A positive result is obtained when the blue color of the aliphatic aldehyde
solution disappears and a brick-red precipitate forms. If the test is negative, the
aromatic aldehyde and simple ketone solution retains its blue color.
Schiff's Test

Procedure
3 to 5 drops of formaldehyde, benzaldehyde, and
acetone were placed in three separate test tubes. Then
add 2 ml of Schiff's reagent to each test tube.

Results and Analysis

The first tube that contains formaldehyde and the second

tube that contains benzaldehyde, when the Schiff's
reagent was added, the reagent color changed into dark
purple. While for the third tube with acetone, the reagent
color changed into pink color.
 Schiff's Test
Chemical Reaction

Discussion
For test tube A, the reagent color changed to dark purple. It shows that
aliphatic aldehyde reacts with Schiff reagent. Test tube B change the
reagent color to pink color. Theoretically, it shows the reaction of an
aromatic aldehyde with a schiff reagent. For test tube C, the reagent colour
remains unchanged. This shows that this test tube contains ketone which are
they cannot react with schiff reagent as it cannot oxidized like aldehyde.
Schiff's Test

Conclusion

For the Schiff Test, the positive result will show by formation of
magenta-pink colour. For the negative result formation of
magenta-pink colour does not happen.

Schiff reagent
 Oxidation

Procedure
potassium permanganate solution and diluted sulfuric acid solution in 3
separated test tubes were mixed. Then, added 0.5 ml of formaldehyde to the
first test tube, 0.5 ml of benzaldehyde to the second test tube, and 0.5 ml of
acetone to the third test tube.

Results and Analysis

The reagent added by formaldehyde shifts color from

purple to a clearer color, added by the benzaldehyde
shifts from purple to a bit clearer with yellowish
precipitate at the top, and added by acetone remained
purple
 Oxidation

Discussion
After mixing KMnO4 and H2SO4:

Test tube A added by formaldehyde, the reagent color changed a clearer form, this shows a
positive reaction, or the mixture of KMnO4 and H2S04 oxidized formaldehyde.

Test tube B added by benzaldehyde, the reagent color changed a to a little bit clear with a
yellowish precipitate at the top, this also shows a positive reaction, or the mixture of KMnO4
and H2S04 oxidized benzaldehyde.

Test tube C added by acetone, the reagent color did not change and remained purple, this
shows a negative reaction, or the mixture of KMnO4 and H2S04 cannot oxidized acetone.
 Oxidation
Conclusion
In this experiment potassium permanganate and diluted sulfuric acid were used as an
oxidizing agent. Potassium permanganate reacts with diluted sulfuric acid and produces
manganese sulfate, potassium sulfate, oxygen, and water. Aliphatic aldehyde
(formaldehyde) and aromatic aldehyde (benzaldehyde) reacts positively with the oxidizing
agent. While simple ketone (acetone) does not show any reaction with the oxidizing agent.

Aldehydes and ketones have varied reactivity to oxidizing agents. Aldehydes are more reactive to
oxidation than ketones because they have a hydrogen atom immediately linked to the carbonyl
carbon.

Ketones, which lack a hydrogen atom on the carbonyl carbon atom, may only be oxidized to a
carboxylic acid under more severe circumstances (stronger reagents and higher temperatures), since
oxidation to an acid necessitates the breakage of a carbon-carbon bond. They will not oxidize under
normal oxidative conditions. Several laboratory procedures that discriminate between aldehydes and
ketones are based on the fact that the two types of chemicals oxidize differently.
Iodoform Test

Procedure
3 test tubes with 1 ml of acetone, benzaldehyde, and

formaldehyde were prepared, then 1.5 ml of 10% NaOH

solution and 0.5 ml of water were added to all test tubes.

lastly, 1 to 5 drops of iodine solution were added and each

test tubes were Acetone Benzaldehyde Formaldehyde

Results and Analysis

When the iodine solution was added to the test tube with acetone in the presence of
NaOH and water; A yellow precipitate was observable.

For both aldehydes in the presence of NaOH and water (benzaldehyde and
formaldehyde), no precipitate nor any signs of reaction happened.
Iodoform Test

Discussion

When iodine and sodium hydroxide are added to a compound, it forms a pale yellow
precipitate of triiodomethane or iodoform if that compound has a methyl ketone.

Conclusion
Iodoform tests are used to identify the structure of a carbonyl compound, thus it can
be used to identify and sometimes differentiate ketones and aldehydes. Acetone had
a positive result while both aldehydes did not because acetone has a methyl ketone
or its carbonyl carbon is attached to a methyl group.
 Process Questions
Which reaction/test

will distinguish

ketones and aldehyde

Tollens’ test is the reaction that is used to distinguish aldehydes from ketones, as
aldehydes are able to be oxidized into a carboxylic acid while ketones cannot. Tollens’
reagent, which is a mixture of silver nitrate and ammonia, oxidizes the aldehyde to a carboxylic
acid.
It takes advantage of the fact that aldehydes, unlike ketones, are easily oxidized. A
positive test result in Tollen's test can be obtained if their is a formation of black or silver
precipitate. If the sample is not an aldehyde, then it will give a negative result.
 Process Questions
How are aldehydes and

ketones used in the

medical field and industry?

Some uses of Aldehydes Some uses of Aldehydes
Formaldehyde is a gas. With 40%
The most common ketone is acetone

solution in water, it forms Formalin which

which is an excellent solvent for a

is used in preserving biological

number of plastics and synthetic fibres.
specimens. In the household, acetone is used as a

When reacted with phenol, formaldehyde

nail paint remover and paint thinner.
forms Bakelite, which is used in plastics,
In medicine, it is used in chemical

coatings, and adhesives. peeling and for acne treatments.

Acetaldehyde is largely used for the Cyclohexanone is another important

production of acetic acid and pyridine

ketone which is primarily used in the

derivatives. production of nylon.

Benzaldehyde is used in perfumes,

cosmetic products, and dyes. It is added

to provide almond flavour to food

products and also used as a bee

repellent.
 References
Farhana, F. (2020,May). REACTIONS OF ALDEHYDE AND KETONE (5,7,10). UNIVERISITI TEKNOLOGI MARA.
https://doi.org/10.1515/9783112375525-025

Libretexts. (2020, September 13). Tollens’ Test. Chemistry LibreTexts.

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Aldehydes_and_
Ketones/Reactivity_of_Aldehydes_and_Ketones/Tollens_Test

Soft Spot For Science. (2021, January 12). Aldehydes and Ketones: Tollen’s Test [Video]. YouTube.
https://www.youtube.com/watch?v=2WEpNqWyUPo

Chemistry edb. (2014, October 5). Using Tollens’ Reagent to Test for Aldehydes (Silver Mirror Test) [Video]. YouTube.
https://www.youtube.com/watch?v=7I-y3I3VzM8&feature=youtu.be

A. (2021, March 22). General Data Protection Regulation(GDPR) Guidelines BYJU’S. BYJUS.
https://byjus.com/chemistry/aldehydes-ketones/#uses-of-aldehydes-and-ketones

A. (2021b, March 22). General Data Protection Regulation(GDPR) Guidelines BYJU’S. BYJUS.
https://byjus.com/chemistry/iodoform-test/