Lab #4

Date: 26/10/2021
Title: Investigating Carbonyl Compounds
Aim: To carry out the stipulated tests to determine which of the samples
of carbonyl compounds is an aldehyde and which is a ketone.
Apparatus and Materials: droppers, test tubes, test tube rack, test tube
holder, matched, 10cm3 measuring cylinders, Samples B,C and D,
Fehling’s reagent, 2,4 –DNPH, aqueous ammonia, aqueous silver nitrate
and distilled water.
Theory:
Carbonyl compounds are organic molecules which contains the carbonyl
functional group (C =O). In this experiment, the two carbonyl groups
focused on are aldehydes and ketones.
The general formula of aldehydes are shown below:

where R is an alkyl group

The general formula of ketones are shown below:

where R is an alkyl group

The carbonyl group (C =O) which is present in both aldehydes and
ketones gives them their reactive nature, hence, distinct colour changes
are seen when they react with specific reagents. However, there are
several differences between these two groups. Aldehydes are more
reactive than ketones, so aldehydes undergo oxidation to form
carboxylic acids whereas ketones cannot be oxidized without breaking
the carbon chain. Aldehyde reactions always occur at the end of the
carbon chain whereas Ketone reactions always occur in the middle of the
chain. With respect to nomenclature, Aldehydes has the suffix- al, while
ketones has the suffix- one.

Procedure:
1. A few drops of 2,4-DNOH was added to a few cm3 of sample B
and the observations were recorded.
2. A few drops of ammonia solution was added to a few cm3 of silver
nitrate and the mixture was shaken until the precipitate dissolved.
A few drops of Sample B was then added to the mixture and the
observations made were recorded.
3. A few drops of sample B was added to a few cm3 of Fehling’s
reagent. The mixture was gently heated and the observations made
were recorded.
4. Steps 1 to 3 were repeated for samples C and D.
5. All results obtained were tabulated.
Diagram:
DIAGRAM SHOWING THE SET UP OF TEST TUBES CONTAINING
SAMPLES B,C AND D DURING EXPERIMENT.
Table of Results:
Table of results showing the observations recorded when samples B,C
and D were tested with three reagents each.

Discussion:
In this experiment, three samples: B, C and D were all tested for the
presence of carbonyl compounds. When these carbonyl compounds were
detected, they were then tested to determine if they were either ketones
or aldehydes. This was done by conducting three different tests on each
sample. These stipulated tests included:2,4 DNPH, Tollen’s reagent and
Fehling’s reagent.
Firstly, all three samples were tested with the organic compound, 2,4-
DNPH (dinitrophenylhydrazine). This reagent is also known as ‘Brody’s
reagent’ and is used to identify ketones and aldehydes using the C=O
bond. When sample B was tested with 2,4 DNPH, the solution remained
orange and no precipitate was formed. This indicated the absence the
carbonyl groups: ketones and aldehydes. On the contrary, when samples
C and D were tested with 2,4 DNPH, both solutions yielded an orange
precipitate, indicating the presence of a carbonyl group such as a ketone
or aldehyde. The formation of this orange precipitate in both solutions
can be accounted for by the ability of the carbonyl groups to react with
the H2 at the end of the 2,4 DNPH molecule. This reaction is known as a
condensation reaction and involves the loss of a water molecule. The
orange precipitate 2,4 dinitrophenylhydrazone is then formed.
The general equation for the above reaction is shown below:

Secondly, the Tollen’s reagent test was carried out on all three samples.
The Tollen’s Test uses the Tollen’s reagent which consists of a solution
of silver nitrate in excess ammonia. This test was used to distinguish
between the two carbonyl compounds, i.e, aldehydes and ketones, which
were detected in the previous test. This is easily distinguishable due to
the fact that aldehydes have the ability to become oxidized into
carboxylic acids while ketones do not.
When samples B and D were tested with Tollen’s reagent, there was a
negative result, i.e, no changes occurred in either sample. As previously,
determined, sample B was neither an aldehyde nor a ketone, hence this
inference remains. Sample D was previously determined to be a
carbonyl compound, however, the negative reaction during the Tollen’s
reagent test indicates that sample D is a ketone because of its inability to
become oxidized. On the contrary, when sample C was mixed with
Tollen’s reagent, a positive result was produced, i.e, a silver mirror was
produced. This indicates that sample C was indeed an aldehyde and
underwent oxidation to form a carboxylic acid. The silver complex ions
[Ag(NH3)2]+ in the Tollen’s reagent were reduced to silver, hence the
silver was seen as a thin reflective layer inside the test tube. This is
described as the ‘silver mirror’.
The half equation for the reduction of the silver complex ion is shown
below:

The equation for the oxidation of the aldehyde is shown below:

The overall balanced equation for this reaction is shown below:

Lastly, the three samples were tested with Fehling’s reagent. The
Fehling’s reagent test is once again used to distinguish between an
aldehyde and a ketone. The Fehling’s test uses the Fehling’s reagent
which consists of two solutions: Fehling’s A (which contain aqueous
Cu2+ ions in the form aqueous copper(II) sulfate) and Fehling’s B
(which contains a complexing agent reagent (tartrate ions) and an alkali).
When aldehydes are heated with Fehling’s reagent, an orange-red
precipitate is formed as these carbonyl compounds have the ability to
become oxidized, whereas a ketone cannot be oxidized.
When samples B and D were heated with Fehling’s reagent, there was a
negative result, i.e, no reaction occurred. As previously determined,
sample B was neither an aldehyde nor a ketone, hence this inference
remains. Sample D however, was determined to be a carbonyl
compound but when mixed with Fehling’s reagent, no reaction occurred.
This indicates that sample D is therefore, a ketone as it did not have the
ability to be oxidized by the Fehling’s reagent. On the contrary, when
sample C was tested with Fehling’s reagent, a positive result was
obtained, i.e, a reaction occurred and a brick red precipitate was formed.
The formation of this precipitate is due to the oxidation of the aldehyde
to a carboxylic acid by the Cu2+ ions. The Cu2+ ions were reduced to the
copper (I) state, hence accounting for the coloured precipitate.
The general equation for the oxidation of an aldehyde to form a
carboxylic acid is shown below:

The reduction of copper is shown below:

Precautions:
1. All apparatus was carefully washed with distilled water to remove
an contaminants.
2. Test tubes were labelled B,C and D to avoid confusion when
recording observations.
3. A white tile was used to observe colour changes.
4. Lab protective gear such as gloves and lab coats were used b
students to prevent any injuries when handling chemicals.

Sources of Error:
 1. Water bath was not heated at a high enough temperature for
reactions to occur.
2. Colour changes were subjective.
Assumptions:
1. If a carbonyl compound was present in the sample, only one was
present in a sample at a time.
2. Reagents used contained no impurities or contaminants.

Reflection:
In this experiment, I have learnt how to properly distinguish between
aldehydes and ketones with respect to their reactions and chemical
structure. I have also been able to improve my laboratory skills such as
handling apparatus, taking accurate observations and making accurate
deductions/inferences.
I have also learnt that aldehydes and ketones are widely used for
everyday purposes due to their oxidizing abilities. For example,
aldehydes such as benzaldehyde is a component used in the production
of perfumes and cosmetic products whereas ketones such as acetone is
commonly known as nail polish remover and can also be used as a paint
thinner. Ketones are also used in the dermatology field to treat acne.

Conclusion:
In conclusion, it was determined that Sample B was neither a ketone nor
aldehyde , Sample C was determined to be an aldehyde and Sample D
was determined to be a ketone.