CHEMICAL LABORATORY I

BSK1402

EXPERIMENT:

Experiment 8: Organic functional group test (aldehydes and ketones)

STUDENT HAJARUL AJIEHAH BINTI ISHAK

MATRIX NO. SA22013
COURSE BSK1402 ORGANIC CHEMISTRY
LABORATORY
SECTION 02
DATE 6/5/2023
ABSTRACT
The aim of this experiment was to identify which functional groups the various
chemicals and unknown substances belonged to using the different reaction tests. The main
purpose was to determine the reactions of Aldehydes and Ketones. Aldehydes and Ketones are
organic compounds consisting of the carbonyl functional group. Aldehydes contain their
carbonyl group at the end of the carbon chain and are susceptible to oxidation while Ketones
contain theirs in the middle of the carbon chain and are resistant to oxidation. The Tollens’s
Reagent test caused the oxidation of aldehydes thus forming a mirror-like image in the test
tube rendering it a positive.

Aldehydes react with Tollens reagent giving a grey-black precipitate or a silver mirror.
Fehling’s solution is a complex compound of Cu2+. When the aldehyde compound is treated
with Fehling’s solution Cu2+ is reduced to Cu+ and the aldehyde is reduced to acids. During
the reaction, a red precipitate is formed.

Aromatic aldehydes do not respond to Fehling’s test. An aqueous solution of the compound
may be used instead of an alcoholic solution. Formic acid also gives this test. Schiff’s reagent
is prepared by passing sulphur dioxide into a solution of the dye fuchsin. The solution
becomes colourless due to the formation of an additional product. Aldehydes abstract
sulphurous acid from Schiff’s reagent and restore the pink colour. y, for the Brady’s Test, the
positive result will form orange precipitate and the negative result did not formed orange
precipitate. Aldehydes and ketones combine with sodium bisulphite to for well-crystallized
water-soluble products known as “aldehyde bisulphite” and “ketone bisulphite”. Aldehydes
and ketones of low molecular weights are volatile compounds. Identification of aldehydes
and ketones is based on two types of reactions, addition reaction to the double bond
and oxidation reaction.

In aldehydes, the carbonyl group is attached to a hydrogen atom and an aliphatic or

aromatic group. Formaldehyde is an exceptional case in which the carbonyl present in
formaldehyde is attached to two hydrogen atoms. In ketones, the carbonyl group is attached
to two aliphatic or aromatic groups.

The difference between ketone and aldehyde is the carbonyl group present in aldehydes
can be easily oxidised to carboxylic acids, whereas the carbonyl group in ketones is not
oxidised easily. This difference in reactivity is the basis for the distinction between aldehydes
and ketones
INTRODUCTION
The carbon-oxygen double bond is one of the most important functional groups, due to its
ubiquity, which are involved in most important biochemistry processes. Reactivity of this
group is ruled by the electron imbalance in the πorbitals of the bond between a more
electronegative and a carbon atom. This carbon atom is more likely to undergo a nucleophilic
attack, especially if the oxygen is protonated. If the carbonyl group has hydrogen’s in the α-
position, it can tautomerize to the enol, thus, Keto tautomer can become Enol
tautomer.Aldehydes and Ketones are organic compounds that consist of the carbonyl
functional group, C=O. The carbonyl group that consists of one alkyl substituent and one
hydrogen is the Aldehyde and those containing two alkyl substituents are called Ketones.
These two organic compounds undergo reactions that are related to the carbonyl group,
however, they can be distinguished due to their “susceptibility to oxidation” The carbonyl of
an aldehyde is always at the end of the carbon chain whereas the carbonyl of a Ketone can lie
anywhere within the carbon chain.
These two organic compounds are found abundantly in nature. Since the carbonyl group
is polar, aldehydes and ketones have a larger dipole moment. In the carbonyl group, the
positive carbon atom will be attacked by nucleophiles. Addition reactions can be undergone by
carbonyl groups. Since Aldehydes have the hydrogen atom attached to it, it makes them more
susceptible to oxidation, which is the loss of electrons. However, Ketones lack the hydrogen
atom in their carbonyl group and are therefore resistant to oxidation. Small Aldehydes and
Ketones are easily dissolved in water but as the chain increases in length, its solubility
decreases.
Aldehyde, is an any of a class of an organic compounds in which a carbon atom shares
a double bond with oxygen atom, a single bond of hydrogen atom and a single bond with
another atom or group of atoms with it. For the example is CH3CHO (ethanal). Ketones is a
carbon that attach with double bond of oxygen, a single bond of R group and another single
bond of R’ group. The structure of ketone is like this RC(=O)R’ where R and R’ can be any
carbon containing substituents. For the example is CH3C(=0)CH3 (propanone). There are
many tests that can be used to determine whether the solution is ketone or aldehyde. The tests
are, Fehling’s Test, sodium bisulfate solution Test, Schiff’s Test, Tollen’s test and Brady’s
Test.

OBJECTIVE
To classify of an organic compound The following carbonyl compounds are provided for the
tests below:
Aldehydes: Propanal and Benzaldehyde
Ketones: Propanone and Acetophenone
METHODOLOGY
1.Brady test

Dissolve about 0.5 mL or 50 mg of the compound to be tested in 2 mL 95% ethanol. Add 2 to

3 drops of this mixture into the test tube containing 3 mL 2,4-dinitrophenylhydrazine reagent
(Brady reagent).* Shake the tube and observe the formation of any precipitate. If no
precipitate forms immediately allow the mixture to stand for 5-10 minutes. Record your
observations. *The 2, 4-dinitrophenylhydrazine reagent can be prepared by dissolving 3 g of
2,4- dinitrophenylhydrazine in 15 mL concentrated sulfuric acid. This solution is added in to a
mixture of 20 mL water and 70 mL 95% ethanol with stirring and filtered.

2.Sodium bisulfate solution test

Add aldehyde or ketone (about 0.2 mL or 2 mg) into a test tube containing 1 mL alcoholic
sodium bisulfite solution.* Plug the test tube with a cork and shake thoroughly. Record any
observations. *The alcoholic sodium bisulfite reagent can be prepared by adding 1 mL ethanol
to 4 mL 40% aqueous solution of sodium bisulfite. The reagent must be filtered before use.

3.Tollen’s test

Add 2-3 drops or 0.1 g of the compound that is to be tested to the Tollens' reagent*. Shake the
tube slowly and note the formation of silver mirror/precipitate for the presence of an aldehyde
group. If there is no precipitate after 10 minutes, warm the mixture in a water bath at 30°C for 5-
10 minutes. Record your observation. *Tollens' reagent can be prepared by adding one drop of
NaOH 10% solution to a 2 mL 5% silver nitrate solution in a test tube. Add ammonia 5%
solution drop by drop until all the precipitate (silver oxide) dissolves. Avoid using excess
ammonia in order to obtain a sensitive reagent (The reagent must be prepared just before use and
should not be stored).

4.Fehling’s test

Dissolve 0.2 g or 1 mL of the compound to be tested in 5 mL water and add 5 mL of the Fehling's
reagent* to the solution. Slowly shake the tube and heat the mixture to boiling. Cool the mixture
to room temperature and note the occurrence of any precipitation. Record your observations.
*Fehling's solution can be prepared as follows:
Solution #1: Dissolve 17.32 g hydrated copper sulphate crystal in 200 mL water and dilute the

5.Schiff’s test

Add 1-2 drops of the compound to be tested to 1 mL Schiff's reagent* in a test tube. Shake it
slowly and observe the color develop in 4-5 minutes. If the compound does not dissolve in the
Schiff's reagent, cap the test tube with a cork and shake it vigorously until an emulsion forms.
Record your observations. *Schiff's reagent is prepared by dissolving 0.005 g p-Rosaline
hydrochloride (Fuchsin) in 50 mL distilled water followed by addition of 2 mL saturated
sodium bisulfite solution. After 1 hour, add 1 mL concentrated hydrochloric acid and then leave
the solution to stand for 24 hours. This reagent is colorless and very sensitive.

RESULT
a) Brady’s test
SOLUTION OBSERVATION

Propanol Bright orange precipitate formed

Benzaldehyde Bright orange precipitate formed

Acetophenone Yellow precipitate formed

Propanone Yellow precipitate formed

 b) Sodium bisulfate solution test
SOLUTION OBSERVATION

Propanol White precipitate formed

Benzaldehyde White precipitate formed

Acetophenone White precipitate formed

Propanone White solution remain unchanged

c) Tollen’s test
SOLUTION OBSERVATION

Propanol Silver mirror colour formed

Benzaldehyde Silver mirror colour formed

Acetophenone No change

Propanone No change

d) Fehling’s test
SOLUTION OBSERVATION

Propanol Brick-red precipitate formed

Benzaldehyde Pink precipitate formed

Acetophenone No change

Propanone No change

e) Schiff’s test
SOLUTION OBSERVATION

Propanol Reagent colour change into pink colour

Benzaldehyde Reagent colour change into pink colour

Acetophenone No change

Propanone No change
DISCUSSION
For brady’s test the equation is ,
 In this experiment , 2 compounds in the test tubes yields positive result when they are
react with 2-4,dinitrophenylhydrazine. And the rest of the test tube which contain propanone
and acetophenone forming yellow precipitate. They are form bright orange precipitate when
Brady’s reagent was added. The compounds is propanol and benzaldehyde which is aldehyde.
This experiment can detect the presence of C=O found in the aldehyde and ketone. It also can
be as confirmation for the unknown solution to know is it either aldehyde or ketone or other
solutions contain in it the test tubes.

For sodium bisulfate solution test , positive result for this test is forming white
precipitate. When propanol ,benzaldehyde and acetophenone react with sodium bisulfate
solution they are forming white precipitate. But when propanone react sodium bisulfate
solution the result is the white precipitate remain umchanged.

The chemical reaction is given below.

For fehling’s test in this experiment , only aldehyde shows positive result as it can turns
the blue colour of fehling’s reagent into brick-red precipitate and pink precipitate. Aromatic
aldehyde did not react with fehling’s reagent as it contaims benzene ring. Due to resonance ,
it becomes a strong bond and oxidizing agent that cuprum unable to oxidize it. Both simple
ketone and cyclic ketone did not undergo fehling’ s test because they cannot be oxidized as
there are no hydrocarbon bond that attach to carbon that contains double bond in ketone.
 For tollen’s test , this test is also called the silver mirror test. Tollens reagent consists of
silver ammonia complex in ammonia solution. Aldehydes react with Tollens reagent giving a
grey-black precipitate or a silver mirror. Always a freshly prepared Tollen’s reagent should
be used. Aldehydes are oxidised to the corresponding acids, and silver in Tollens reagent is
reduced from +1 oxidation state to its elemental form. Generally, ketones do not respond to
this test.

RCHO + 2[Ag(NH3)2]OH → R-COONH4 + 3NH3 + H2O + 2Ag↓(silver mirror)

Apart from aldehydes some other compounds also respond to Tollen’s test, but the presence
of aldehydes is confirmed when the given substance shows a positive test for Tollen’s test,
but if the given compound passes 2,4-dinitrophenylhydrazine test.

The Schiff test is an early organic chemistry name reaction developed by Hugo Schiff and is
relatively general chemical test for detection of many organics that has also found use in the
staining of biological tissues. The Schiff reagent is the reaction product of a dye formulation
such as fuchsin and sodium bisulfite; pararosaniline(which lacks an aromatic methyl group) and
new fuchsin(which is uniformly mono-methylated ortho to the dye's amine functionalities) are
dye alternatives with comparable detection chemistry .For this experiment, 2 – 3 drops of
Schiff ’s reagent is added into 4 test tubes which contains propanol , benzaldehyde , propanone and
acetophenone respectively. All test tubes are shaken gently. For propanol, the light yellowe colour of the
Schiff ’s reagent changes into pink with no emulsion. For benzaldehyde , the light yellow colour of the
Schiff ’s reagent changes into pink with an emulsion . . For acetophenone and propanone , the light
yellow colour of the Schiff ’s reagent changes into colourless solution Theoretically, an aldehyde
reacts with Schiff ’s reagent to produce a pink colour which is a positive result while ketones
do not react with Schiff ’s reagent. Therefore, it can be said that there was an error in this
experiment which may be caused by an expired Schiff ’s reagent or accidentally mixing other
substance into the test tube or the test tube is not cleaned properly and thoroughly.

CONCLUSION
 In conclusion , aldehydes and ketones are utilized in many mechanism and reagents. The
current experiment utilized information known about aldehydes and ketones to identify an
unknown compound. The brady test , the sodium bisulfate solution test , the fehling’s test ,
the tollen’s test and the schiff’s test was utilized to identify the presence of an aldehyde or
ketone respectfully , in the compound which is the compound is propanol , benzaldehyde ,
acetophenone and propanone. As conclusion , we can classify the organic compound. The
difference between aldehydes and ketones are the presence of a hydrogen atom attached to
the carbon-oxygen double bond in the aldehyde. It is because ketone do not have that
hydrogen. The presence of that hydrogen atom makes aldehydes very easy to oxidize and
makes it as a strong reducing agent. In conclusion, it can be deduced that propanone and acetophenone
is a ketone while propanol and benzaldehyde an aldehyde by using qualitative analysis from Brady’s Test,
Fehling’s Test, Tollens’ Test , sodium bisulfate solution test and Schiff ’s Test. Propanol and
benzaldehyde which is an aldehyde is more reactive than acetophenone and propanone which
is a ketone. This is caused by the functional group of the aldehyde which contains a hydrogen
atom and an alkyl group that makes it less stable than ketone which does not have the
hydrogen atom but instead 2 alkyl groups..
APPENDICES

SCHIFF’S TEST BRADY TEST

TOLLEN’S TEST FEHLING’S TEST

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