FACULTY OF SCIENCE

UNIVERSITI TUNKU ABDUL RAHMAN

BACHELOR OF SCIENCE (HONOURS) – BIOCHEMISTRY

YEAR 1, TRIMESTER 2

UDEC1164 – ORGANIC CHEMISTRY

EXPERIMENT 7 – PROPERTIES OF ALDEHYDES AND

KETONES

NAME: LIM WEY LOON

STUDENT ID: 2207600

PARTNER NAME: CHAI HUI QUAN, TAN XUE YI

STUDENT ID: 2207457, 2204645

PRACTICAL GROUP: P1

PRACTICAL DATE & TIME: 14 MARCH 2023

9.00AM - 11.30AM

LAB INTRUCTOR: DR. SIM KOOI MOW

Title of Experiment: Experiment 7 – Properties of Aldehydes and Ketones

Objectives:

1. To test the properties of alcohols, aliphatic and aromatic aldehydes and ketones.
2. To differentiate between alcohols, aliphatic and aromatic aldehydes and ketones.
3. To determine the relation between structure and reaction to iodine-iodide reagent.
4. To determine the class of compounds and possible structure of unknown A, unknown
B and unknown C.

Introduction:

Carbonyl compounds are compounds containing a carbonyl group (-C=O). These

compounds are among those important compounds of organic chemistry including aldehydes
and ketones. The carbonyl group is a functional group containing a double bond between a
carbon atom and an oxygen atom. Generally, carbonyl compounds are polar in nature as some
atoms carries a partial positive charge while some carries a partial negative charge. However,
these compounds are found insoluble in water. Common reactions of carbonyl groups include
nucleophilic addition and substitution (Byju’s, 2023).

Figure 1: General structure of a carbonyl compound

Aldehyde is a class of organic compound in which one side of the carbon of the
carbonyl group is bonded to a hydrogen atom through a single bond. The other side is also
singly bonded to another atom or groups of atoms, generally designated as R. Many
aldehydes have pleasant odours and are derived from alcohols by dehydrogenation (March,
2022). Aldehydes have both IUPAC system names and common names. In the IUPAC
system, aldehydes are named with -al as the suffix. Examples are methanal with two
hydrogen atoms bonded to the carbonyl carbon, ethanal with one methyl group and one
hydrogen atom bonded to the carbonyl carbon. The common names have the suffix -
aldehyde. For example, formaldehyde is the common name of methanal and acetaldehyde is
the common name of ethanal (LibreTexts Chemistry, 2021).
 Ketones are organic compounds which the carbonyl carbon is bonded to two groups
of atoms (not hydrogen atom). They can be synthesised by a wide variety of methods due to
the relative stability and high reactivity of ketones (Brown, 2023). Ketones also have both
IUPAC systems name and common names. In the IUPAC system, ketones are named with
-one as the suffix. Examples are propanone with two methyl groups bonded to the carbonyl
carbon and 2-pentanone with a propyl group and a methyl group bonded to the carbonyl
carbon. The common names have the name of substituent follow by the suffix ketone. For
instance, acetone is the common name of propanone and methyl propyl ketone is the common
name of 2-pentanone (LibreTexts Chemistry, 2021).

Carbonyl compounds can be used as solvent. For instance, acetone is a suitable

solvent for lacquer, acetylene, plastics and varnishes as well as in the manufacture of
pharmaceuticals. Butanone is used as an industrial solvent with similar functions compared to
acetone (ChemLibre Texts Chemistry, 2021). Formaldehyde is used in the manufacture of
plastics and is used for preservations in laboratories (Byju’s, 2023).

Chemicals/ Reagents:

Acetaldehyde, benzaldehyde, acetophenone, 3-pentanone, isopropyl alcohol, unknown A,

unknown B, unknown C, chromic acid solution, Tollen’s reagent, nitric acid, 3M sodium
hydroxide solution, 5% sodium hydroxide solution, Fehling’s solution, Brady’s reagent,
iodine-iodide reagent, 1,4-dioxane

Glasswares:

Test tubes
Experimental Procedure:

A) Chromic acid test

1. To 1 mL portions of acetaldehyde, benzaldehyde, acetophenone, 3-pentanone and

isopropyl alcohol in the separate dry test tube, 1 mL of chromic acid solution was
added.
2. Any changes in colour were observed.
3. The above procedures were repeated with the unknown A, B and C and observations
were made.
B) Tollen’s test

1. A set of test tubes was cleaned by adding 5 - 10 mL of 3M sodium hydroxide to

each and heating them in a water bath.
2. The cleaned test tubes of sodium hydroxide solution were empty, they were rinsed
with distilled water and 2 mL of Tollen’s reagent was added to each tube.
3. 1 mL of acetaldehyde, benzaldehyde, acetophenone, 3-pentanone and isopropyl
alcohol were added to each test tube.
4. The tubes were set aside for a few minutes without agitating the contents. If no
reactions occurred, the mixture was warmed briefly in a water bath.
5. The above procedures were repeated with the unknown A, B and C and observations
were made.
6. At the end of the reaction, excess Tollen’s reagent was promptly destroyed with a
few drops of nitric acid.
7. A drop of nitric acid also could be used to remove silver mirrors from the test tubes.

C) Fehling’s test

1. To 1 mL portions of acetaldehyde, benzaldehyde, acetophenone, 3-pentanone and

isopropyl alcohol in separate dry test tubes, 6 drops of Fehling’s solution were
added.
2. The test tubes were heated in a hot water bath for several minutes.
3. A positive test for an aldehyde would be indicated by a reddish precipitate of Cu2O.
4. The above procedures were repeated with the unknown A, B and C and observations
were made.
D) 2,4-dinitrophenylhydrazine (Brady’s reagent)

1. To 1 mL portions of acetaldehyde, benzaldehyde, acetophenone, 3-pentanone and

isopropyl alcohol in separate dry test tubes, 2 mL of Brady’s reagent was added and
shaken vigorously.
2. If no precipitate formed immediately, they were warmed and allowed to stand for 5-
10 minutes.
3. The presence of a carbonyl compound was indicated by a crystalline precipitate.
4. The above procedures were repeated with the unknown A, B and C and observations
were made.

E) Iodoform test

1. To 1 mL portions of acetaldehyde, benzaldehyde, acetophenone, 3-pentanone and

isopropyl alcohol in separate dry test tubes, 2 mL of water was added.
2. If it was insoluble in water, 1, 4-dioxane was added and swirled at a time until a
homogenous solution was formed.
3. 2 mL of 5% NaOH solution was added, swirled and dropwise potassium iodide-
iodine reagent was added until a deep red-brown colour persists.
4. The resulting mixture was heated in a water bath at 60 oC, adding dropwise
additional iodide/iodine solution if necessary to get the red-brown colour to persist
for at least 2 minutes.
5. They were removed from the water bath, and sufficient 5% NaOH was added
dropwise to cause the disappearance of the red-brown colour and cooled to room
temperature.
6. A yellow precipitate formed was recorded within 15 minutes.
7. The above procedures were repeated with the unknown A, B and C and observations
were made.
Results:

A) Chromic acid test

Compound Observation Deduction

Acetaldehyde Solution turns green Aliphatic aldehyde and
Benzaldehyde Solution remains orange secondary alcohol can be
Acetophenone Solution remains orange oxidised by chromic acid.
3-Pentanone Solution remains orange Aromatic aldehyde and ketones
Isopropyl alcohol Solution turns green cannot be oxidised by chromic
Unknown A Solution remains orange acid.
Unknown B Solution remains orange
Unknown C Solution turns green
Table 1: Chromic acid test

Figure 2: From left to right are reactions of acetaldehyde, benzaldehyde, acetophenone,

3-pentanone, isopropyl alcohol, unknown A, unknown B and unknown C towards chromic
acid soluton.
B) Tollen’s test

Compound Observation Deduction

Acetaldehyde Silver mirror formed before heating Aldehyde shows
Benzaldehyde Silver mirror formed before heating positive results in
Acetophenone Silver mirror formed after heating Tollen’s test before
3-Pentanone Silver mirror formed after heating heating. Ketones and
Isopropyl alcohol Silver mirror formed after heating alcohols show positive
Unknown A Silver mirror formed before heating result in Tollen’s test
Unknown B Silver mirror formed after heating after heating.
Unknown C Silver mirror formed after heating
Table 2: Tollen’s test

Figure 3: From left to right are reactions of acetaldehyde, benzaldehyde, acetophenone,

3-pentanone, isopropyl alcohol, unknown A, unknown B and unknown C towards Tollen’s
reagent.
C) Fehling’s test

Compound Observation Deduction

Acetaldehyde Red-brown precipitate formed Aliphatic aldehyde
Benzaldehyde No precipitate formed gives positive result in
Acetophenone No precipitate formed Fehling’s test. Aromatic
3-Pentanone No precipitate formed aldehyde, ketones and
Isopropyl alcohol No precipitate formed alcohols show negative
Unknown A No precipitate formed results in Fehling’s test.
Unknown B No precipitate formed
Unknown C No precipitate formed
Table 3: Fehling’s test

Figure 4: From left to right are reactions of acetaldehyde, benzaldehyde, acetophenone,

3-pentanone, isopropyl alcohol, unknown A, unknown B and unknown C towards Fehling’s
solution.
D) 2,4-dinitrophenylhydrazine (Brady’s reagent)

Compound Observation Deduction

Acetaldehyde A yellow precipitate is formed When reacting with Brady’s
Benzaldehyde A yellow precipitate is formed reagent, aldehydes form a
Acetophenone An orange precipitate is formed yellow precipitate while
3-Pentanone An orange precipitate is formed ketones form an orange
Isopropyl alcohol A clear orange solution is formed precipitate. Alcohols show
Unknown A A yellow precipitate is formed negative results when reacting
Unknown B An orange precipitate is formed with Brady’s reagent.
Unknown C A clear orange solution is formed
Table 4: Reaction with Brady’s reagent

Figure 5: From left to right are reactions of acetaldehyde, benzaldehyde, acetophenone,

3-pentanone, isopropyl alcohol, unknown A, unknown B and unknown C towards Brady’s
reagent.
E) Iodoform test

Compound Observation Deduction

Acetaldehyde Yellow precipitate is formed Only aldehydes or ketones
Benzaldehyde No precipitate is formed
Acetophenone Yellow precipitate is formed with the structure or

3-Pentanone No precipitate is formed alcohols with the structure

Isopropyl alcohol Yellow precipitate is formed

Unknown A No precipitate is formed show positive
Unknown B Yellow precipitate is formed results in iodoform test.
Unknown C No precipitate is formed
Table 5: Iodoform test

Figure 6: From left to right are reactions of acetaldehyde, benzaldehyde, acetophenone,

3-pentanone, isopropyl alcohol, unknown A, unknown B and unknown C towards
iodide/iodine reagent.

Discussion:

The chemical equations for chromic acid test are as follows:

1. Acetaldehyde:
3CH3CHO + 2H2CrO4 +6H+ 3CH3COOH + 2Cr3+ + 5H2O
2. Isopropyl alcohol:
3(CH3)2CHOH + 2H2CrO4 +6H+ 3(CH3)2C=O + 2Cr3+ + 8H2O

Chromic acid, H2CrO4, is a strong acid and a reagent for oxidizing alcohols to
ketones and carboxylic acids. Secondary alcohols are oxidized to ketones. It will also oxidise
an aldehyde to a carboxylic acid (LibreTexts Chemistry, 2023a). The oxidation of aldehydes
occurs through the reversible nucleophilic addition of water to the carbonyl to form a gem-
diol functional group. Ketones do not have hydrogen atom attached to their carbonyl carbons,
they are resistant to oxidation. Only very strong oxidizing agents such as potassium
manganate (VII) (potassium permanganate) solution oxidize ketones (LibreTexts Chemistry,
2023b). Benzaldehyde cannot be oxidised by chromic acid as it cannot form a stable gem-diol
group in water (Adi Chemistry, n.d.).

The mechanism of oxidation of acetaldehyde by chromic acid:

The mechanism of oxidation of isopropyl alcohol by chromic acid:

(LibreTexts Chemistry, 2023)

 The chemical equations for Tollen’s test are as follows:

1. Acetaldehyde:
CH3CHO + 2Ag(NH3)2OH +OH- CH3COO- + 2Ag + 4NH3 + 2H2O
2. Benzaldehyde:
C6H5CHO + 2Ag(NH3)2OH +OH- C6H5COO- + 2Ag + 4NH3 + 2H2O
3. Isopropyl alcohol:
(CH3)2CHOH + 2Ag(NH3)2OH (CH3)2C=O + 2Ag + 4NH3 + 2H2O

Tollen’s reagent, which was initially discovered by a German chemist Bernhard

Tollens is the chemical reagent that is used in the Tollen's test to determine the presence of
aldehyde functional groups along with some alpha-hydroxy ketones in an unknown solution.
It is a colourless, aqueous solution consisting of a silver ammonia complex in an ammonia
solution. Aldehyde gives a grey-black precipitate or a silver mirror when freshly prepared
Tollens' reagent is added to the solution. In the reaction, the silver ion goes from +1 oxidation
state to 0 oxidation state or elemental state, thereby getting reduced and oxidizing the
aldehyde to its respective acid. Therefore, the reaction involved is a redox reaction. Since the
reaction occurs in an alkaline medium therefore carboxylic acid isn't obtained directly;
instead, carboxylate ion is obtained (Vedantu, 2023). As ketones do not have a hydrogen
atom bonded to the carbonyl carbon, ketones are not oxidised by Tollen’s reagent. Therefore,
the positive result may indicate that the test tubes contain some other chemicals that are
oxidised by Tollen’s reagent.

The mechanism of Tollen’s test of acetaldehyde and benzaldehyde:

where R represents CH3 in acetaldehyde and C6H5 in benzaldehyde (Chemistry Learner, n.d.).
In hydroxide medium, the final product exist in carboxylate ion.
 The chemical equations for Fehling’s test are as follows:

1. Acetaldehyde:
CH3CHO + 2Cu2+ +5OH- CH3COO- + Cu2O + 3H2O

Fehling’s solution is prepared by combining two separate solutions: Fehling A and

Fehling B. Fehling A is a blue-coloured aqueous solution of copper (II) sulphate (CuSO4).
Fehling B is a colourless aqueous solution of potassium sodium tartrate
(KNaC4H4O6·4H2O, also known as Rochelle salt) in an alkaline base like sodium hydroxide
(NaOH). The two solutions are individually prepared and later mixed to give Fehling’s
solution, which is blue. When aldehydes are added to Fehling’s solution, they are easily
oxidized by the bistartratocuprate (II) complex. During this process, copper (II) ions get
reduced to copper (I) ions leaving a red precipitate of copper (I) oxide (Cu 2O) (Chemistry
Learner, n.d.). Benzaldehyde is an aromatic aldehyde and the carbonyl group is an electron
withdrawing group. Therefore, the carbonyl group pulls the electron from the electron-rich
benzene ring. Due to this reason, the polarity of the C−H bond in the carbonyl group is
reduced as the C−H bond now has a higher electron density. Thus, the C−H bond becomes
stronger as polarity of a bond becomes less, the bond becomes stronger (Vedantu, 2023b).
Since the reaction with Fehling’s solution is an oxidation, ketones do not show positive
results. On the other hand, Fehling’s solution is a weaker oxidising agent, unable to oxidise
alcohols to carboxylic acids or ketones.

The mechanism of Fehling’s test of acetaldehyde:

(Chemistry Learner, n.d.)

 The chemical equations for Brady’s test are as follows:

1. Acetaldehyde
CH3-(C=O)-H + C6H3(NO2)2NHNH2 C6H3(NO2)2NHN=CHCH3 + H2O
2. Benzaldehyde
C6H5-(C=O)-H + C6H3(NO2)2NHNH2 C6H3(NO2)2NHN=CHC6H5 + H2O
3. Acetophenone
C6H5-(C=O)-CH3 + C6H3(NO2)2NHNH2 C6H3(NO2)2NHN=C(CH3)C6H5 + H2O
4. 3-Pentanone
C2H5-(C=O)-C2H5 + C6H3(NO2)2NHNH2 C6H3(NO2)2NHN=C(C2H5)2 + H2O

2,4-dinitrophenylhydrazine is a C-nitro compound that is phenylhydrazine substituted

at the 2- and 4-positions by nitro groups as shown in Figure 7. It has a role as a reagent
(National Center for Biotechnology Information, 2023). When an organic compound
containing carbonyl functional group reacts with Brady's reagent, then a yellow or orange, or
red-coloured precipitate is formed. This precipitate is a derivative of 2,4-
dinitrophenylhydrazine and is called 2,4-dinitrophenylhydrazone. If the organic compound is
aliphatic, then the colour of the precipitate is towards yellow, and for an aromatic organic
compound, the colour is towards red. The amino group of 2,4-dinitrophenylhydrazine acts as
the nucleophilic and adds to the carbonyl group. A water molecule is eliminated in this
reaction. Therefore, this reaction is an example of nucleophilic addition-elimination and also
of the condensation reaction (Chegg.com, n.d.).

Figure 7: Structure of Brady’s reagent, 2,4-dinitrophenylhydrazine

The mechanism of Brady’s test for acetaldehyde, benzaldehyde, acetophenone and 3-

pentanone are as follows:
 In reaction of acetaldehyde, the R is a methyl group and R’ is a hydrogen atom while
in benzaldehyde, the R represents a phenyl group and R’ is a hydrogen atom. In the reaction
of acetophenone, the R is a phenyl group while the R’ represents a methyl group. In 3-
pentanone, both R and R’ represents ethyl group (Chegg.com, n.d.).

The chemical equations for iodoform test are as follows:

1. Acetaldehyde:
CH3CHO + 3I2 + 4OH- HCOO- + CHI3 + 3I- + 3H2O
2. Acetophenone:
C6H5COCH3 + 3I2 + 4OH- C6H5COO- + CHI3 + 3I- + 3H2O
3. Isopropyl alcohol:
(CH3)2CHOH + 4I2 + 6OH- CH3COO- + CHI3 + 5I- + 5H2O

The iodoform test is used to determine whether a given unknown chemical contains
carbonyl compounds (such as aldehydes and ketones) with the structure R-CO-CH3 or
alcohols with the structure R-CH(OH)-CH3 (Clark, 2004). A pale yellow precipitate of
iodoform is formed when iodine and sodium hydroxide solutions are added to the chemical
containing the structure mentioned above.

The mechanism of Iodoform test of acetaldehyde and acetophenone are as follows

where R represents a hydrogen atom for acetaldehyde, and, a phenyl group in acetophenone:
 (Kare, 2022)

Precaution Steps:

1. The test tubes used should be dry.

2. All the tests must be conducted under fume hood as the chemicals possess an
unpleasant smell.
3. Avoid touching sodium hydroxide solution, as it is a strong alkaline.
4. Avoid touching any phenolic compound as they are corrosive and cause severe
chemical burns on contact.
5. Avoid brining alcohol near the flame as it is highly flammable.
6. The Tollen’s reagent is explosive on standing for long periods of time; therefore, the
reagent is prepared fresh just before it is needed.
7. Do not delay destroying the Tollen’s reagent after finishing the test as the Tollen’s
reagent can form an explosive fulminate on standing.
8. The excess Tollen’s reagent cannot be placed together with other chemical waste.
9. Avoid adding excessive 1,4-dioxane during the experiment.
Conclusion:

In the oxidation by chromic acid, aliphatic aldehyde and secondary alcohol can be
oxidised by chromic acid. Aromatic aldehyde and ketones cannot be oxidised by chromic
acid.

In the reaction with Tollen’s reagent, aldehyde shows positive results in Tollen’s test
before heating. Alcohols show positive result in Tollen’s test after heating. Ketones
theoretically show negative results, therefore, indicating a mistake in this experiment.

In the reaction with Fehling’s solution, aliphatic aldehyde gives positive result in
Fehling’s test. Aromatic aldehyde, ketones and alcohols show negative results in Fehling’s
test.

When reacting with Brady’s reagent, aldehydes form a yellow precipitate while
ketones form an orange precipitate. Alcohols show negative results when reacting with
Brady’s reagent.

Only aldehydes or ketones with the structure or alcohols with the structure

show positive results in iodoform test.

Unknown A is not oxidised by chromic acid, form silver mirror before heating in
Tollen’s test, shows negative result in Fehling’s test, forms yellow precipitate when reacting
with Brady’s reagent and shows negative result in iodoform test. Hence, unknown A is an
aromatic aldehyde.

Unknown B is not oxidised by chromic acid, form silver mirror after heating in
Tollen’s test, shows negative result in Fehling’s test, forms orange precipitate when reacting
with Brady’s reagent and shows positive result in iodoform test. Therefore, unknown B is a

ketone, with the structure .

Unknown C is oxidised by chromic acid, form silver mirror after heating in Tollen’s
test, shows negative result in Fehling’s test, shows negative results when reacting with
Brady’s reagent and shows negative result in iodoform test. Hence, unknown C is not an
aldehyde or ketone .
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