Name: Diane Princess N.

Sultan Date: March 6, 2023

Section: BioSc 2A Group No.4

EXPERIMENT 4

ALDEHYDES AND KETONES

OBJECTIVE:

After the experiment, the students are expected to:

- Distinguish aldehydes and ketones through various tests.

- Determine the behavior of the two carbonyl-containing compounds (acetone and benzaldehyde)
when exposed to open air by oxidation.
- Qualitatively identify the oxidation rate of the four compounds when exposed to potassium
permanganate solution.
- To identify which of the compounds contained aldehydes by Fehling’s test.
- Check the presence of carbonyl groups in the compounds by phenylhydrazone test.
- Check the presence of one methyl group immediately attached to the carbonyl carbon in the
aldehyde or ketone sample by iodoform test.

Prelaboratory Assignment:

1. Define the following terms: oxidation, reducing agents, oxidizing agents.

• Oxidation
o The process or result of oxidizing or being oxidized
• Reducing agents
o One of the reactants of an oxidation-reduction reaction which reduces the other reactant by giving
out electrons to the reactant.
• Oxidizing agents
o Is a chemical substance which causes another chemical species to lose electrons. Oxidation
means the loss of electrons, the loss of a hydrogen atom, or the addition of an oxygen atom.

2. Identify two oxidizing agents to be used in this experiment.

 3. Draw the structure of the following compounds: ethanal, benzaldehyde, propanone, and
acetophenone.

ethanal Propanone

PROCEDURE FLOWCHART
4. In a table form, write the reagents used in each test, the probable carbonyl compounds positive to
these reagents and the expected results.

Reagents used Probable C=O Expected Results

Compounds + to
Reagents

Oxidation rate Potassium Acetaldehyde, Purple color fades

(KMnO4) permanganate, benzaldehyde, away.
acetaldehyde, acetone, Dark brown
acetone, acetophenone precipitate forms.
benzaldehyde,
acetophenone

Fehling’s Test Copper (II) sulphate Acetaldehyde, Brick red

(Fehling A), benzaldehyde precipitate forms.
Potassium sodium
tartrate w/ Sodium
hydroxide (Fehling
B), acetaldehyde,
acetone,
benzaldehyde,
acetophenone
Phenylhydrazone Phenylhydrazine, Acetaldehyde, Orange-yellow
Derivative (Brady’s water, glacial acetic acetone, precipitate forms.
Test) acid, acetaldehyde, benzaldehyde,
acetone, acetophenone
benzaldehyde,
acetophenone

Iodoform Test Potassium iodide Acetaldehyde, Light yellow

(KI), Sodium acetone, precipitate forms
hypochlorite (NaClO), acetophenone
acetaldehyde,
acetone,
benzaldehyde,
acetophenone

Tollens’ Test Ammoniacal silver Acetaldehyde, Dark grey precipitate

nitrate, benzaldehyde or silver mirrors
acetaldehyde, form.
acetone,
benzaldehyde,
acetophenone

Schiff’s Test Silver nitrate, sodium Acetaldehyde, Pinkish color

hydroxide, benzaldehyde develops.
ammonium
hydroxide,
acetaldehyde,
acetone,
benzaldehyde,
acetophenone

Benedict’s Test Benedict’s solution acetaldehyde, Green precipitate -

(Sodium citrate, acetone, traceable reducing
pentahydrate of benzaldehyde, sugars.
copper (II) sulfate, acetophenone Yellow precipitate
sodium carbonate), - small amount of
acetaldehyde, reducing sugars.
acetone, Orange-red
benzaldehyde, precipitate -
acetophenone moderate amount.
Brick-red precipitate
- high amount.
 OBSERVATIONS AND RESULTS:

For every sample of aldehydes and ketones tested, mark √ for positive reaction, and indicate the visible
evidence observed. For negative reaction, mark X.

SAMPLES
TESTS

Ethanal Benzanal Propanone Phenylethanone

✔ ✔ ✘ ✘
Tollen’s Test

✔ ✘ ✘ ✘
Fehling’s Test

✘ ✘ ✔ ✔
Iodoform Test

✔ ✔ ✘ ✔
Oxidation
Rate

Observations:

I. Tollens’ test

Initial Final

Ethanal formed white -yellow formed silver mirror

precipitate

Benzanal formed white precipitate formed silver mirror

Propanone (Acetone) No reaction; colorless No changes were observed

solution

Acetophenone Dark-brown bubbles settled No changes were observed

at the bottom

Note: the presence of silver mirror indicates a positive result

II. Fehling’s Test

 Before heating After heating

Ethanal Less clear, more foggy blue formed a reddish-brown

solution precipitate

Benzanal White bubbles floating on top Clear, deep blue solution

of the blue solution

Propanone (Acetone) No reaction; remained deep Clear, deep blue solution

blue solution

Acetophenone No reaction; remained deep Clear, deep blue solution

blue solution

Note: formation of reddish-brown precipitate indicates positive result

III. Iodoform Test

Before heating After heating

Ethanal Clear, reddish-brown solution Dark orange solution

Benzanal Clear, golden brown solution Dark yellow solution with

black liquid settled at the
bottom

Propanone (Acetone) Foggy, pale yellow solution Less foggy, pale yellow
solution, formation of yellow
precipitate that settled at the
bottom

Acetophenone Foggy, yellow solution Clear, colorless solution,

formation of yellow precipitate
that settled at the bottom

Note: formation of yellow precipitate indicates positive result

IV. Oxidation

Observation

Ethanal Turned dark orange after 23 seconds

Benzanal Muddy brown, formation of black precipitate after 30 seconds

Propanone (Acetone) No oxidation

Acetophenone Slightly darker with white precipitate after 40 seconds

QUESTIONS

Determine if the following substances will have a positive or negative result with the following tests. √ if positive
and X if negative

Substances Fehlings Tollens Iodoform Oxidation

✔ ✔ x
Propanal

Diphenylmetha x
none

Cyclohexyl
hexanone

x x?
3-pentanone

✔ ✔
heptanal

DISCUSSION

Aldehydes and ketones are two types of organic molecules that include the carbonyl group.
RCH(=O) is the structure of aldehyde, whereas R2C(=O) is the structure of a ketone. The carbonyl
group in aldehydes is connected to a hydrogen atom as well as aliphatic or aromatic radicals.
Formaldehyde is an unusual example in which two hydrogen atoms are bonded to the carbonyl
carbon in the compound. Two aliphatic or aromatic groups are attached to the carbonyl group in
ketones. (Vedantu, 2021)

In this experiment, the students conducted five (5) experiments in the aim of distinguishing
aldehydes and ketones: Oxidation by air (OA), Oxidation by Potassium Permanganate (OPP),
Fehling’s Test (FT), Phenylhydrazone test (PT), and Iodoform test (IT). The sample carybonyl-
containing compounds used in OA were acetone and benzaldehyde. In the remaining four (4)
tests, equal volumes of four (4) different carbonyl-containing compounds, the acetaldehyde
(aldehyde), acetone (ketone), benzaldehyde (aldehyde), and acetophenone (ketone) were put
into different test tubes and were subjected to the said tests.

The aim of OA was to compare the behavior of the two carbonyl-containing compounds (acetone
and benzaldehyde) when exposed to open air. After the conduct of the test, upon observation,
results showed that acetone was negative to any changes, whereas benzaldehyde, over time,
converted into colorless crystals as it was exposed to air. Acetone, a ketone, didn’t respond
positively to OA because ketones are highly resistant to oxidation due to the lack of a hydrogen
atom attached directly to the carbonyl carbon, unless acted upon by very strong oxidizing agents.
Benzaldehyde, on the other hand, responded well with OA due to the presence of a hydrogen
atom that makes it more susceptible to nucleophilic addition. (Vendatu, 2021) In the oxidation of
benzaldehyde, benzoic acid forms in the appearance of colorless crystals (Sankar, et al., 2014).
The aim of OPP was to qualitatively identify the oxidation rate of the four compounds when
exposed to potassium permanganate solution. A control tube of dilute permanganate solution was
prepared. The test yielded the four compounds in different tubes positive, represented by the
diminished violet color of the solution after shaking, and the formation of dark brown precipitates.
The solution in the control tube remained violet. All the samples responded positively because
potassium permanganate is a strong oxidizing agent that can even oxidize ketones, which are
difficult to oxidize by milder oxidizing agents, therefore, it has a wide spectrum of efficacy in
oxidizing compounds. (Vedantu, 2021) As it oxidizes compounds, it forms a dark brown-colored
manganese dioxide (MnO2) which stains anything that is organic. (Vedantu, 2019)

FT was used to identify which of the compounds contained aldehydes. The test yielded only the
acetaldehyde positive, and the benzaldehyde negative even though it is an aldehyde, contrary to
what was predicted in PreLab #4. When the aldehyde compound is treated with Fehling’s solution,
Cu2+ is reduced to copper I oxide which forms the red precipitate, and the aldehyde is reduced
to acids. (ByJu’s, 2019) However, for benzaldehyde, even if it is an aldehyde, it maintained a
bluish color, the same with acetone and acetophenone ketones, because aromatic aldehydes and
ketones naturally don’t respond to Fehling’s solution. (ByJu’s. 2020) Ketones, particularly, are
mostly resistant to oxidation.

PT was also used to check the presence of carbonyl groups in the compounds. All compounds
responded positively to PT and formed orange precipitates because they, as all aldehydes and
ketones do, contain atleast one C=0 group. Otherwise, the compounds would’ve remained clear,
without the formation of precipitates. (ByJu’s, 2019)

IT was used to check the presence of one methyl group immediately attached to the carbonyl
carbon in the aldehyde or ketone sample. (Vendatu, 2019) Of the four compounds, only
benzaldehyde solution cleared out and did not produce a light-yellow precipitate, and the
acetaldehyde, acetone, and acetophenone produced a cloudy solution with light yellow
precipitates. Only benzaldehyde was negative, and the other three compounds were positive.
This is due to the structures of the compounds, which are illustrated in PreLab #3. Benzaldehyde
lacked a methyl group (CH3) attached immediately to its carbonyl carbon, whereas acetaldehyde,
acetone, and acetophenone had their methyl group attached to its carbonyl carbon. Only
acetaldehyde of all aldehydes gives a positive IT because it is the only aldehyde with a methyl
group attached immediately to its carbonyl group.
 CONCLUSION:

It is concluded that:

● Benzaldehyde oxidizes but acetone does not by mere open-air oxidation.

● All the four compounds are oxidizable by potassium permanganate.
● Only acetaldehyde, of the four compounds, is reactive to Fehling’s test.
Benzaldehyde, although an aldehyde, is unreactive because it is an
aromatic aldehyde.
● All the compounds contain carbonyl groups.
● Benzaldehyde does not react in iodoform test because it does not contain a methyl
group

REFERENCES

ByJu’s. (2019). Fehling Test. ByJu’s. https://byjus.com/chemistry/fehling-test/

ByJu’s. (2019). Tests for Aldehydes and Ketones. ByJu’s.

https://byjus.com/chemistry/tests-for-aldehydes-and-ketones/

ByJu’s. (2019). Iodoform Test. ByJu’s. https://byjus.com/chemistry/iodoform-test/ ByJu’s.

(2020). Fehling's Solution. ByJu’s. https://byjus.com/jee/fehlings-solution/

Sankar, M., Nowicka, E., Carter, E. et al. The benzaldehyde oxidation paradox explained by the
interception of peroxy radical by benzyl alcohol. Nat Commun 5, 3332 (2014).
https://doi.org/10.1038/ncomms4332

Vedantu. (2019). KMnO4 - Potassium Permanganate. Vedantu.

https://www.vedantu.com/chemistry/potassium-permanganate

Vedantu. (2020). Fehling Test. Vedantu. https://www.vedantu.com/chemistry/fehling-test

Vedantu. (2020). Benedicts Test. Vedantu. https://www.vedantu.com/chemistry/benedicts-test

Vedantu. (2021). Test for Aldehydes and Ketones. Vedantu.

https://www.vedantu.com/chemistry/test-for-aldehydes-and-ketones

Youtube links:
https://www.youtube.com/watch?v=4B4xKZhiYIc
https://www.youtube.com/watch?v=Ea4gz-7Cpao
https://www.youtube.com/watch?v=iCDS0dVZUL8