Al-Qadisiyah University

College of Pharmacy

‫إعداد الطلبة‬
‫علي عبد الحسين عبادي‬
‫رسل عادل حليم‬

Identification of ‫اسيل فرحان عبود‬

‫زهراء سلطان كاظم‬

Aldehydes and ‫مريم عطية فرحان‬

‫رسل محسن كاظم‬

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Ketones ‫براء جواد عبد الكاظم‬
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(Group B3)
 Identification of Aldehydes and Ketones 1
1- Introduction:
Aldehydes and ketones have a carbonyl group (C = O) as a functional group. A
ketone has two alkyl or aryl groups attached to the carbonyl carbon (RCOR'). The
simplest ketone is acetone, which has two methyl groups attached to the carbonyl
carbon (CH3COCH3).

An aldehyde is similar to a ketone, except that instead of two side groups connected
to the carbonyl carbon, they have at least one hydrogen (RCOH). The simplest
aldehyde is formaldehyde (HCOH). An aldehyde differs from a ketone by having a
hydrogen atom attached to the carbonyl group. This makes the aldehydes very easy
to oxidize. For example, ethanal, CH, CHO, is very easily oxidized to either ethanoic
acid, CH₂COOH, or ethanoate ions, CH₂COO-. Ketones don't have that hydrogen
atom and are resistant to oxidation. They are only oxidized by powerful oxidizing
agents which have the ability to break carbon - carbon bonds.
 Identification of Aldehydes and Ketones 2
2- Physical and chemical properties:
2.1- Physical properties:
▪ Methanal is a gas at room temperature, ethanal boils close to room temperature
(21°C) and all other aldehydes and ketones are liquid at room temperature.
(Formalin, an aqueous solution of 40 % formaldehyde and 15 % methanol.) or as
one of its solid polymers: paraformaldehyde, (CH₂O)n, or trioxane, (CH₂O)3.
▪ The boiling point of aldehydes and ketones is higher than that of alkanes and
ethers of similar molecular mass, however, it is significantly less compared to
that of alcohols and carboxylic acids due to the absence of H-bonding in
aldehydes and ketones. They are colorless except benzaldehyde, which has a pale
yellow colour (due to oxidation) with a characteristic odour.
▪ The lower members of aldehydes and ketones such as methanal, propanone etc.
are miscible with water in all proportions because they form hydrogen bond with
water. As the length of the alkyl chain increases, the solubility of aldehydes and
ketones decreases rapidly because number of carbon atoms increases in chain.
▪ All aldehydes and ketones are fairly soluble in organic solvents like benzene,
ether, methanol, chloroform etc.
▪ Aliphatic aldehydes and ketones burn with a blue flame (without smoke) while
aromatic ones burn with a yellow smoky flame.

2.2- Chemical properties:

▪ All reactions of aldehydes and ketones are related to the carbonyl group.
▪ Aldehydes contain a hydrogen atom attached to its carbonyl while ketones don’t.
This difference in the chemical structure affects their chemical properties in two
ways:
a) aldehydes are easily oxidized to the corresponding acids and have reducing
properties while ketones are not oxidized under similar conditions and do not
show reducing properties.
b) aldehydes are usually more reactive than ketones towards nucleophilic
addition, the characteristic reaction of carbonyl group.

▪ Both aldehydes and ketones are neutral compounds that don’t change the color of
litmus paper.
 Identification of Aldehydes and Ketones 3
3- Practical work:
Both aldehydes and ketones give yellow or orange precipitate with 2,4-
dinitrophenylhydrazine reagent.

Procedure:
Take 2-3 drops of the liquid compound in a test tube or in case of solid compound,
dissolve a few crystals of it in 2-3 mL alcohol. Add a few drops of an alcoholic
solution of 2,4-dinitrophenylhydrazine. Appearance of yellow, orange or orange-red
precipitate confirms the presence of carbonyl group. If precipitate does not appear at
room temperature, warm the mixture in a water bath for a few minutes and cool.

Distinction between aldehydes and ketones can be done on the basis of Schiff’s
test, Fehling’s test and Tollen’s test are given by aldehydes only.

1. Tollen's test:
Tollen’s reagent is the combination of silver nitrate solution with ammonium
hydroxide in the presence of sodium hydroxide solution. Aldehydes show
positive result with this reagent because the reaction between them involves the
oxidation of the aldehyde to the corresponding carboxylic acid with an
accompanying 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.

Procedure:
▪ Take 1 mL of freshly prepared (~ 2 %) silver nitrate solution in a test tube.
Add 1-2 drops of sodium hydroxide solution to it and shake, a dark brown
precipitate of silver oxide appears. Dissolve the precipitate by adding
ammonium hydroxide solution drop-wise.
▪ To the above solution, add an aqueous or an alcoholic solution of the organic
compound.
▪ Heat the reaction mixture of step (2) in a water bath for about 5 minutes.
Formation of a layer of silver metal on the inner surface of the test tube which
Identification of Aldehydes and Ketones 4
shines like a mirror, indicates the presence of an aldehyde.

2. Fehling's reagent:
Only aldehydes can reduce Fehling’s reagent (a deep blue solution) to give a
red cuprous oxide precipitate.

Procedure:

Take nearly 1 mL of Fehling’s solution A (is an aqueous copper sulphate

solution) and 1 mL of Fehling’s solution B (is an alkaline solution of sodium
potassium tartarate (Rochelle’s salt)) in a clean dry test tube. To this add 2-3 drops
of the liquid compound or about 2 mL of the solution of the solid compound in
water or alcohol. Heat the content of the test tube for about 2 minutes in a water
bath. Formation of brick red precipitate of copper (I) oxide indicates the presence
of an aldehyde. This test is not given by aromatic aldehydes.

3. Schiff’s test:
The Schiff test is a chemical test used to check for the presence of aldehydes
in a given analyte. This is done by reacting the analyte with a small quantity of a
Schiff reagent (which is the product formed in certain dye formulation reactions
such as the reaction between sodium bisulfite and fuchsin).

Procedure:

Take 3-4 drops of the liquid compound or dissolve a few crystals of organic
compound in alcohol and add 2-3 drops of the Schiff’s reagent. Appearance of
pink colour indicates the presence of an aldehyde.
 Identification of Aldehydes and Ketones 5
Reference:
[1] ©NCERT, “Tests for Functional groups in Organic compounds”, (2018).
[2] Azhar M. Jasim, Duraid H. Mohammad, “A Laboratory Manual on Practical
Organic Chemistry for 2nd year students”, (2012).