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Experiment No. 8
ALDEHYDES and KETONES

Name: _Maej Marie J. Oraga_____________ Date Performed: _03/25/2021_____

Section: __BSN- A__________________ Date Submitted: __03/27/2021____

IV. Data and Observation

Table 1. Odor
(Based on research)
Test Samples Observation
Has a strong, fruity odor
Acetaldehyde

Benzaldehyde Has an almond-like odor

Acetone Smells like nail polish remover

Acetophenone Sweet, strong odor

Table 2a. Oxidation with KMnO4

Test Samples Observation
After 5 minutes of intermittent shaking, from light yellow, the mixture turned
Acetaldehyde transparent or colorless.
After 5 minutes of intermittent shaking, from reddish brown the mixture
Benzaldehyde turned brown in color.

After 5 minutes of intermittent shaking, from light purple, the mixture turned
Acetone reddish pink in color.

After 5 minutes of intermittent shaking, from reddish brown, the mixture

Acetophenone turned dark brown in color.

Chemical equations:
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Table 2b. Fehling's Test

Test Samples Observation
After warming in a water bath, from bright blue, the mixture turned murky
Acetaldehyde
brown in color.

Benzaldehyde After warming in a water bath, the mixture remained bright blue in color.

Acetone After warming in a water bath, the mixture remained bright blue in color.

Acetophenone After warming in a water bath, the mixture remained bright blue in color.

Chemical equations:

Table 2c. Tollen's Test

Test Samples Observation
At first, there were no observable changes in the mixture aside from the
Acetaldehyde tiny forms of bubbles situated at the bottom, but after the warm water
bath, the mixture turned blackish brown in color.
At first, there were no observable changes in the mixture aside from the
tiny forms of bubbles situated at the bottom, but after the warm water
Benzaldehyde
bath, the mixture turned faded and cloudy white in color with small dark
particles forming at the bottom of the tube.
There were no observable changes in the mixture aside from the tiny
Acetone
forms of bubbles situated at the bottom at first.
At first, there were no observable changes in the mixture aside from the
Acetophenone tiny forms of bubbles situated at the bottom, but after the warm water
bath, the mixture turned blackish brown in color.
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Chemical equations:

Table 3. Iodoform Test

Test Samples Observation

Acetaldehyde After 2 drops of 10% NaOH, the color of the iodine disappeared

After 2 drops of 10% NaOH, the color of the iodine disappeared and yellow
Benzaldehyde
crystalline precipitates formed at the bottom of the tube.

Acetone After 2 drops of 10% NaOH, the color of the iodine disappeared.

After 2 drops of 10% NaOH, the color of the iodine disappeared and yellow
Acetophenone
crystalline precipitates formed at the bottom of the tube.
Chemical equations:
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Table 4. 2,4-DNPH Test

Test Samples Observation
The mixture was brownish yellow in color but there were only little to no
Acetaldehyde
yellow precipitates that formed.

The mixture was brownish yellow orange in color and there was an
Benzaldehyde
obvious amount of yellow precipitates that formed.

The mixture was brownish yellow in color and there was an obvious
Acetone
amount observable yellow precipitates that formed.

The mixture was bright yellow orange in color and there was an obvious
Acetophenone
amount observable yellow precipitates that formed.
Chemical equations:

Table 5. Schiff's Test

Test Samples Observation

Acetaldehyde The mixture turned dark magenta pink in color.

Benzaldehyde The mixture turned pale magenta pink in color.

Acetone The mixture turned bright red orange in color.

The mixture turned bright orange in color and there were precipitates that
Acetophenone
formed and resided at the bottom as well.
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Chemical equations:

Table 6. Reaction with NaHSO3

Test Samples Observation
The mixture was colorless and there were no observable white
Acetaldehyde
precipitates that formed.

The mixture was colorless and there were a number of observable white
Benzaldehyde
precipitates that formed.

The mixture was colorless and there were no observable white

Acetone
precipitates that formed.

The mixture was colorless and there were a few observable white
Acetophenone
precipitates that formed.
Chemical equations:
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Table 8. Aldol Formation

Test Samples Observation

Acetaldehyde The mixture turned murky white in color and cloudy in appearance.

Benzaldehyde The mixture turned white in color and cloudy in appearance.

The mixture turned white with a hint of pale brown in color and slightly
Acetone
cloudy in appearance.

The mixture turned white with a hint of pale red in color and slightly
Acetophenone
cloudy in appearance.
Chemical equations:

V. Questions
1. Give the composition of the following reagents used:
a) Fehling’s reagent
Fehling's reagent consists of two solutions. Solution A contains 7% CUSO4 and solution B
contains 25%KOH and 35% sodium potassium tartrate.

b) Tollen’s reagent
Tollen’s reagent consists of a solution of silver nitrate, ammonia and some sodium
hydroxide.

c) Schiff’s reagent
Schiff’s reagent consists of Basic Fuchsin Hydrochloride: 1%, Hydrochloric Acid: 1%, Sodium
Metabisulfite: 1% and water: 98%
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2. Which is more easily oxidizable, aldehydes or ketones? Why or why not?

Aldehydes are more easily oxidizable and this is because of the presence of a hydrogen atom
attached to the carbon-oxygen double bond in the aldehyde. Ketones, unfortunately do not
have that hydrogen attached.

3. What is the structural requirement of the following reactions?

a) Iodoform Reaction
This type of reaction requires the presence of a CH3CH(OH) group in alcohols.
b) Aldol condensation
This type of reaction requires an aldehyde or ketone that contains at least one a-
hydrogen and a carbonyl of another molecule under basic or acidic conditions.

4. Suggest a simple chemical test that will differentiate between an aldehyde and a ketone. Tabulate your
answers.

The Tollen’s test can be considered as a simple chemical test that will differentiate an aldehyde and a
ketone. It focuses on the attribute that aldehydes are readily oxidized while ketones are not. The
Tollen’s test oxidizes the aldehyde into carboxylic acid while ketones resist oxidation

5. What specific type of reaction will carbonyl compounds undergo when treated with 2,4-DNPH, NaHSO3,
semicarbazide or alcohol?

Based on research, the specific type of reaction that carbonyl compounds undergo when treated with
2,4-DNPH, NaHSO3, semicarbazide or alcohol is called Nucleophilic addition.

6. Show the mechanism of the reaction between an aldehyde with 2,4-DNPH as a typical example.

Aldehydes and ketones undergo a reaction known as 2,4-DNP test or Brady's test. The mechanism of this
goas as: in its reaction with aldehydes and ketones, for example, methanol, 2,4-dinitrophenylhydrazine
form a yellow, orange or red precipitate. This reaction helps to differentiate and identify aldehydes and
ketones from other compounds.