FAKULTI SAINS GUNAAN

UNIVERSITI TEKNOLOGI MARA

CHM301 - ORGANIC CHEMISTRY II

EXPERIMENT : REACTIONS OF ALDEHYDE AND KETONES

GROUP : AS1204D
LECTURER’S NAME : DR. ZATI ISMAH BINTI ISHAK
DATE OF SUBMISSION : 11/4/2023
STUDENT’S NAME 1. AUNI AINSHAHARIEAH BINTI ABDUL RAHMAN
(2021866904)

2. NIK NUR INTAN SYAZLEEN BINTI MOHD IDHAM

3. NURUL ADIRA FAZIRA BINTI SALLEH (2021832634)

4. NUR SAFIYYA BINTI MOHD NAWI (2021819554)

Declaration of Academic Honesty

Academic honesty or academic integrity is a very important virtue that all students should
uphold at all times.

I/We declare that the lab report submitted is not plagiarised and is entirely my/our own work,
and that no part of it has been copied from any work produced by another person(s)/
source(s)or provided by any other student(s).

I/We understand that issuing a false declaration can result in severe penalties and I/we
am/are willing to be penalized if any form of copying is found valid.
 EXPERIMENT 2 : REACTIONS OF ALDEHYDE AND KETONES

INTRODUCTION

Ketone has a usual structural formula of R-COH and R-COR. Carbonyl group

C=O can also be seen in both of these classes where the carbon atom and oxygen

atom are bonded with a double bond. The carbonyl group is polarized with carbon

atoms that have a slightly positive charge and oxygen atom with a slight negative

charge due to the fact that oxygen has a higher electronegativity. Thus, physical

properties and chemical properties of aldehyde and ketone are strongly influenced

by the polarization of the carbonyl group.

This resulted in aldehyde and ketone being vulnerable to attacks by the

nucleophile at the carbon atom and electrophile at the oxygen atom. A lower boiling

point than alcohol will be achieved when aldehyde and ketone will not form hydrogen

bonds. Aldehyde is easy to be oxidized to produce carboxylic acid which indicates it

to be a strong reducing agent while ketone on the other hand, is not easy to be

oxidized. This is because ketone can only be oxidized by prolonged heating and a

very strong oxidizing agent.

OBJECTIVE

- To study the reactions of aldehyde and ketones.

Observation

Test
Methanal Ethanal Propanone

Tollen’s test The colourless Colorless solution No reaction

solution turned to turns to a light occurred

a greyish solution grey solution with

with grey black precipitate.

precipitate. Light grey solution

Silver mirror was turned to silver

formed. mirror solution.

Fehling’s test

- The blue colour - Solution has a - No changes

solution changed blue colour before occurred.

to a colorless turning colorless. - Blue solution

solution. - Brick-red remains the same.

- Brick-red precipitate has

precipitate formed. formed.

Schiff reagent The colorless

- solution turned to -

a dark purple

(magenta)

solution.
 Reaction with Purple solution The colourless Solution remain

𝐾𝑀𝑛𝑂4 changed to brown solution turned to unchanged

solution with black a red solution.

precipitate before Red solution

turning colourless. turned into a

colourless

solution.

Condensation with The colourless Yellowish-orange

2,4 - DNPH solution turned to crystalline

a yellow solution. precipitate was

Yellow solution formed

- turned to an

orange solution

with orange

precipitate.
DISCUSSION

This experiment’s main objective is to observe the reactions of aldehyde and

ketone. Foremost, aldehyde and ketone are organic compounds which have a

carbonyl group (C=O) as the functional group. These two compounds can be

differentiated by the chemical formula and the chemical structure of the compound.

For instance, if either one of the substituents is hydrogen, the compound is known to

be an aldehyde whereas for ketone, neither of the substituents will consist of

hydrogen.

- Tollen’s Test

Tollen’s reagent is a moderate oxidising agent that can selectively oxidise

aldehydes to their corresponding acids before being reduced to elemental silver

precipitate, which forms a silver mirror coating on the container/test tube walls. The

main purpose of this test is to identify the presence of aldehyde in a compound.

When aldehyde is added, carboxylic acid will be obtained from being oxidised.

From this experiment, based on the observation, for methanal, the colorless

solution changes to a greyish colour solution with grey precipitate at the bottom of

the test tube. Silver mirror was formed at the end of the test. Hence, this indicates

that there was a presence of aldehyde.

For the ethanal, the colourless solution turns to light grey solution with black

precipitate and then turns to silver mirror solution. It is because the silver ion

undergoes a change from 1+ to 0 oxidation states during the process, becoming

reduced and oxidized the aldehyde to the corresponding acid. As a result, the

involved process is a redox solution. A black precipitate is formed along with the
silver mirror solution when the Tollen’s reagent is used. This is a positive test for the

aldehydes. As for propanone, no reactions have been observed. Thus, this indicates

that propanone is a ketone and not aldehyde, which is why there were no reactions

recorded. This can be observed from the equations below :

General formula when metal reacts with Tollen’s Reagent:

𝑂
||
𝑅 − 𝐶 − 𝑂𝐻 + 2𝐴𝑔 + 4𝑁𝐻3 + 2𝐻2𝑂

- Fehling’s Test

Aldehyde and ketone functional groups are distinguished using Fehling’s

solution. Ketones won’t react to the test (apart from hydroxy ketones). For methanal

and ethanal, the blue solution of Fehling’s was decolourised which means it turns to

a colorless solution with brick-red precipitate forming at the bottom of the test tube.

This happens due to the fact that aldehyde will be oxidized then from carboxylate

anion. Thus, aldehyde will give positive results with Fehling’s test. However, for

propanone, no changes occurred upon the observation where the blue colour of the

solution remained unchanged. This indicates that propanone is a ketone which is

known to be giving negative results for the Fehling’s test. Ketones are not ready to

be oxidized compared to aldehydes as the H atom is not directly attached to the

carbonyl group of the compound. These reactions was shown in the equations

below:
General formula when aldehyde react with Fehling’s solution:

2+ − −
𝑅𝐶𝐻𝑂 − 2𝐶𝑢 + 5𝑂𝐻 −−−−−−−> 𝑅𝐶𝑂𝑂 + 𝐶𝑢2𝑂 + 3𝐻2𝑂

- Schiff Reagent

A chemical test called the Schiff’s test is performed to determine whether an

analyte contains aldehydes. This is accomplished by reacting a tiny amount of the

analyte with a Schiff’s reagent. For the ethanal, the colourless solution turns to dark

purple solution. However, as Schiff reagent is mixed with a solution that contains

aldehyde, it will return back to its original colour which is dark purple. Complex

chemicals that are formed are what produces the colour. Aldehydes restore the

magenta colour by removing sulfuric acid from the Schiff’s reagent. Furthermore, as

for methanal and propanone, no observations were recorded for this particular test

as propanone was known to be ketone.

Schiff reagent’s test for aldehydes:

(Schiff Test - Checking for Aldehydes With Schiff Reagent, n.d.)

𝐾𝑀𝑛𝑂4 will exhaustedly oxidise organic compounds up until carboxylic acids

are produced. Aldehydes will be oxidised to carboxylic acid as a result of the

oxidation of alcohols to carbonyls (aldehydes and ketones). For ethanal, the

colourless solution turns to a red solution and then turns back to a colourless

solution again. All of this happens due to the reduction of manganese permanganate

to manganese dioxide. The σ and π bonds of the double bond system are both

destroyed when ozone oxidizes alkenes. The term ozonolysis refers to this cleavage

of an alkene double bond, which is often performed in good yield. As for methanal,

the initial purple solution has changed to brown solution with precipitate before being

colorless at the end. This indicates that methanal is an aldehyde as being known

only aldehyde will have a reaction with 𝐾𝑀𝑛𝑂4 . This particular thing happened

because this reaction is a redox reaction where Mn7+ is reduced to Mn4+ which is a

manganese (IV) oxide. Thus, this is the reason for the colour changes in the solution

and the forming of the precipitates. This suggested that both methanal and ethanal

have positive results for this test.

From the observations, propanone produces no reactions where the purple solution

remains unchanged. The reason is that propanone is a ketone and will not be

oxidized by the potassium permanganate due to the fact that there is no hydrogen

atom attached to the C=O bond. Hence, the test shows a negative result. The

equations below shows the reaction :

−
Methanal : 𝐻𝐶𝐻𝑂 + 2𝑀𝑛𝑂4⁻ + 𝐻2𝑂 −−−> 𝐻𝐶𝑂𝑂𝐻 + 2𝑀𝑛𝑂2 + 2𝑂𝐻
 −
Ethanal : 𝐶𝐻3𝐶𝐻𝑂 + 2𝑀𝑛𝑂4⁻ + 𝐻2𝑂 −−−> 𝐶𝐻3𝐶𝑂𝑂𝐻 + 2𝑀𝑛𝑂2 + 2𝑂𝐻

Propanone : No reaction

- Condensation with 2,4 - dinitrophenyl hydrazine

2,4 - dinitrophenyl hydrazine (DNPH, Brady’s reaction, Borche’s reagent) is

the chemical molecule C6H3(NO2)2NHNH2. Solid dinitrophenylhydrazine comes in

a variety of colours. A yellow colour formation indicates there is a presence of a

carbonyl group in the compound. The test becomes successful when a precipitate in

the colours of yellow, orange or red occurs. An aromatic carbonyl compound causes

an orange precipitate to form when the compound is present. An aliphatic carbonyl

precipitates out as a yellow substance. Ethanal contains either aldehydes or ketones

in it. As for propanone, a yellowish substance was produced in the test tube. This

shows that it is either aldehyde or ketone which are the carbonyl compounds

because of the presence of yellow colour compounds and the formation of the

orange precipitate at the end of the test. However, in order to differentiate between

aldehyde and ketone, other specific tests have to be carried out. The reactions was

portrayed in the equations below :

2-3-dinitrophenylhydrazine reaction with ethanal:

(2,4 DNP Test (2,4-Dinitrophenylhydrazine)[C6H3(NO2)2NHNH2] - Brady's Reagent,

Synthesis, Structure With Examples, n.d.)

1. Describe your observations if you differentiate 2-butanone and

2-methylbutanal using Tollen’s reagent and 𝐾𝑀𝑛𝑂4 .Write the equation

involved.

𝑂
|| 𝐴𝑔(𝑁𝐻3)2⁴

𝐶𝐻3 − 𝐶 − 𝐶𝐻2 − 𝐶𝐻3 −−−−−−−−−> No reaction

2-butanone 𝐻2𝑂

2-butanone react with Tollen’s reagent

𝑂 𝑂
|| 𝐴𝑔(𝑁𝐻3)2⁴ ||

−
𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻 − 𝐶 − 𝐻 −−−−−−> 𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻 − 𝐶 − 𝑂 +𝐴𝑔↑

| 𝐻2𝑂 |

𝐶𝐻3 𝐶𝐻3

2-methylbutanal

2-methylbutanal react with Tollen’s reagent

The equation indicates that 2-butanone does not react with Tollen’s reagent.

Thus, no silver mirror was produced due to the ketone because of its structure.

Hence, the H-atom in 2-butanone is not chemically bonded to the carbonyl group.

This is why 2-butanone is difficult to oxidise. A silver mirror is produced by the

reaction of Tollen’s reagent and 2-methylbutanal. This is because 2-methylbutanal is

more easily oxidised because the H-atom is directly connected to the carbonyl

group.
 𝑂
|| 𝐾𝑀𝑛𝑂4

𝐶𝐻3 − 𝐶 − 𝐶𝐻2 − 𝐶𝐻3 −−−−−−−> No reaction

2-butanone

2-butanone react with KMn𝑂4

𝑂 𝑂

|| 𝐾𝑀𝑛𝑂4 ||

𝐶𝐻3 − 𝐶𝐻2 − 𝐶𝐻 − 𝐶 − 𝐻 −−−−−−> 𝐶𝐻 − 𝐶𝐻 − 𝐶𝐻 − 𝐶 − 𝑂𝐻

| |

𝐶𝐻3 𝐶𝐻3

2-methylbutanal
2-methylbutanal react with KMn𝑂4

The equation indicates that only 2-methylbutanal react with KMn𝑂4.

Carboxylic acids are produced during the oxidation of aldehyde. Nonetheless, the

end product of 2- methylbutanal is 2-methylbutanoate. In addition, due to ketone’s

resistance to oxidation and lack of the hydrogen atom necessary for the oxidation

process, there is no reaction between KMn𝑂4.for 2-butanone.

1. Test tube has to be rinsed with distilled water before starting another test.

2. Skin contacts and eye contact need to be avoided while handling the

chemicals.

3. Each of the chemicals need to be measured carefully based on the

procedures provided.

CONCLUSION

From the experiment, it can be concluded that the interactions between

ketone and aldehyde can be examined by utilising different tests. Aldehyde and

ketone can be distinguished using the Tollen’s test, Fehling’s test, Schiff reagent test,

reaction with KMn𝑂4 and condensation with 2,4 - DNPH. So, throughout the

experiment, we can determine propanone is ketone meanwhile ethanal and

methanal are aldehyde.

Chemistry Learner. (2020, April 17). Schiff Reagent: Definition, Formula, and

Preparation. Chemistry Learner.

https://www.chemistrylearner.com/schiff-reagent.html

Cliffsnote. (n.d.). Alkenes: Oxidation and Cleavage Reactions. Www.cliffsnotes.com.

https://www.cliffsnotes.com/study-guides/chemistry/organic-chemistry-i/reaction

s-of-alkenes/alkenes-oxidation-and-cleavage-reactions

Reusch, W. (2013). Carbonyl Reactivity. Msu.edu.

https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm

Vedantu. (2023, April 1). Tollens Reagent - Preparation | Tollens Test. Www.vedantu.com.

https://www.vedantu.com/chemistry/tollens-reagent

Schiff Test - Checking for Aldehydes with Schiff Reagent. (n.d.). Byju's. Retrieved

April 10, 2023, from https://byjus.com/chemistry/schiff-reagent-and-test/

2,4 DNP Test (2,4-Dinitrophenylhydrazine)[C6H3(NO2)2NHNH2] - Brady's Reagent,

Synthesis, Structure with Examples. (n.d.). Byju's. Retrieved April 10, 2023,

from https://byjus.com/chemistry/2-4-dinitrophenylhydrazine/

BOOKS

1. Denis, W. G. (1907). On the Behavior of Various Aldehydes, Ketones and

Alcohols Towards Oxidizing Agents .... Amerika Syarikat: Press of the

Eschenbach printing Company.

2. Organic Chemistry: Problems and Solutions. (2019). (n.p.): MJP Publisher.