A.

Title : Identification of Aldehydes and Ketones Groups

B. Purpose :
1. Identify organic compounds that contain aldehyde groups
2. Identify organic compounds that contain ketone groups
3. Distinguish between aldehyde groups and ketone groups contained in
organic compounds
C. Materials :
 5% NaOH (Sodium hydroxide)
 Isopropyl alcohol (2-propanol)
 I2 (Iodine)
 AgNO3 1% (IUPAC: Silver(I) nitrate, Trivial: Silver nitrate)
 2% NH4OH (Ammonium Hydroxide)
 [Ag(NH3)2]NO3 (IUPAC: Diamminesilver(I)nitrate, Trivial: Tollens
reagent)
 C7H6O (IUPAC: Benzaldehyde)
 Acetone (IUPAC: Propanon)
 Cyclohexanon
 Fehling Reagent
 Aquades
 Phenylhidrazin
 Methanol (Trivial: Methyl alcohol)
 Ethanol (Trivial: Ethyl alcohol)
 Formaline (IUPAC : metanal Trivial: formaldehid)
 Acetaldehyde ( IUPAC name : etanal, Trivial name : acetaldehyde)
 Hydrochloric acid
D. Procedure
1. Tollens Test
Making of tollens reagents
Purpose: To make tollens reagent
 1 ml of solution AgNO3 1%

- Put into a test tube that has been washed with soap, water, and dried

- Added 1 ml of 5% NaOH solution

- Mixed

- Added drop by drop 2% NH4OH solution while being shaked until

the precipitate dissolve

Tollens reagents

Reaction:
2AgNO3 (aq) + 2NaOH  Ag2O (s)  + 2NaNO3 (aq) + H2O (l)
Ag2O (s)  + 2NH4OH (aq)  2Ag(NH3)2OH (aq)
Tollens Test
Purpose: To identify organic compound containing aldehyde and
ketones groups.
1 ml reagent tollens

- Put into a test tube

- Added 2 drops of benzaldehyde to the test tube

- Shaked the mixture and leave it for 10 minutes

- If no reaction occurs the test tube is placed in hot water (350 – 500)

for 5 minutes

- The observation result are recorded

Result

Reaction :
O O

CH COH

+ 2Ag(NH3)2OH (aq)  + 2Ag (s)

+ 2NH3 (aq) +H2O (l)
 2 drops of cyclohexanone

1. Added 1 mL Tollens
reagent
2. Shaken the mixture and let
it still for 5 minutes
3. If the reaction doesnt occur
put the test tube into hot
water (35oC-50oC) for 5
minutes
4. Noted the result
Result
Reaction:

(aq) +2Ag(NH3)2OH (aq)

2 drops of acetone

1. Added 1 mL Tollens
reagent
2. Shaken the mixture and let
it still for 5 minutes
3. If the reaction doesnt occur
put the test tube into hot
water (35oC-50oC) for 5
minutes
4. Noted the result
Result
Reaction:

+ 2Ag(NH3)2OH (aq)
 1 ml reagent tollens

- Put into a test tube

- Added 2 drops of formalin to the test tube

- Shaked the mixture and leave it for 10 minutes

- If no reaction occurs the test tube is placed in hot water (350 – 500)

for 5 minutes

- The observation result are recorded

Result

Reaction:

O O

H C H (aq) + 2Ag(NH ) OH (aq)  H

3 2
C ONH4 + 2Ag (s) +

3NH3 (aq) + 2H2O (l)

2. Fehling Test
Purpose: The purpose of the fehling and benedict test is to identify
aldehyde groups with the fehling and benedict test.

5 ml of benedict reagents or
5 ml of newly made fehling
reagents
- Put into a test tube

- The test tube is placed in boiling water (3-4 minutes heating

process) and observe the change that occur 10-15 minutes

- Tested on formaldehyde

Result
 5 mL of Fehling Reagent

1. Put into a test tube

2. Added some drops of acetone
3. Put test tube in boiling water (3-
4 minutes of heating process)
4. Observed the changes that
occurs in 10-15 minutes

Result

Reaction: CH3COCH3(aq) + 2Cu2+(aq) + 5OH-(aq) →

5 mL of Fehling Reagent

1. Put into a test tube

2. Added some drops of
cyclohexanon
3. Put test tube in boiling water (3-
4 minutes of heating process)
4. Observed the changes that
occurs in 10-15 minutes

Result

Reaction:

+ 2Cu2+(aq) + 5 OH-(aq) →
 3. Bisulfite Addition

5 ml saturated solution of sodium bisulfate

- Put into erlenmeyer

- The solution is cooled the solution in water (Noted

the temperature)

- 2,5 ml acetone is added into in erlenmeyer

- Let stand 5 minutes

- 10 ml of technical ethanol is added to start mixing

- The reaction result are Filtrated with a filter funnel

Residue Filtrate

- Put Into a test tube

- Added a few drops of HCl concentrated until dissolve

- Noted that happened

Result

Reaction :

ethanol
Na2SO3 (aq) + (aq) (aq)

(aq) + HCl (aq)  (aq) + NaCl

(s) + SO2 (g)
 4. Testing with Phenylhidrazine
Purpose: To identify aldehyde and ketone compounds through testing
with phenylhidrazin
Test Tube 1
2,5 mL of phenylhidrazine

- Entered into test tube

- Added 10 drops of benzaldehyde

- Closed test tube

- Shaken up strongly as long as 1-2 minutes until

the results are crystallize

- Filtered phenylhidrazine that crystallize with

funnel

Residue (crystal) Filtrate

- Washed crystal with a few cold water

- Crysrtallized again with a few methanol or

ethanol

- Let the crystal dry

- Determined the melting point

Result
Reaction :

(aq) + (aq) 
 (s) + H2O (l)

Test Tube 2

2,5 mL of phenylhidrazine

- Entered into test tube

-Added 10 drops of cyclohexanone
- Closed test tube
- Shaken up strongly as long as 1-2 minutes
until
the results are crystallize
- Filtered phenylhidrazine that crystallize with
funnel

Residue (crystal) Filtrate

- Washed crystal with a few cold water

- Crysrtallized again with a few methanol or
ethanol
- Let the crystal dry
- Determined the melting point

Result

Reaction :
 (aq) + (aq) 

(s) + H2O (l)

5. Haloform Reaction
Purpose: To identify organic compounds by using iodoform reactions from the
haloform test
Test Tube 1

3 ml NaOH solution 5%
- Added 5 drops acetone

- Added 10 ml iodine solution while shaked until

the color of iodine is no longer gone. Yellow

iodoform settles.

- Noted the smell.

Result

Reaction :
O O

CH3 C CH3
(aq) + 3I2 (aq) + 3OH- (aq)  CH3 C CI3
(aq) +
3H2O (l) + 3I- (aq)
O O

CH3 C CI3
(aq) + OH- (aq)  CH3 C O
(aq) + CHI3 (aq)
Test tube 2
3 mL of 5% NaOH solution
- Added 5 drops of isopropyl alcohol
- Added 10 mL of iodine solution and shaked
until the color of iodine is no longer gone
- Noted the smell

Result

Reaction:

(aq) + 3I2 (aq) + 3OH- (aq)  (aq) +3H2O (l) +

3I- (aq)

(aq) + OH- (aq)  (aq) + CHI3 (aq)

6. Aldol Condensation
Purpose: To identify aldehyde groups through aldol condensation

4 ml NaOH solution 1%

- Put into a test tube

- Added 0,5 ml acetaldehyde
- Shaked
- Noted the smell
- Boiled the mixture for 3 minutes
- Noted rancid smell from the results of condensation

Result

Reaction:
 O O

NaO
CH3 C H
(aq) + CH3 C H
(aq)
OH O

CH3 C CH2 C
H
H (aq)

Reaction Mechanism that occurs

O O
- -
OH
CH3 C H H 2C C H
O O O
-
CH3 + H 2C  CH3
C H C H C CH2 C H

CH3 C CH2 C H heat

-
O OH

H3C CH CH C H

crotonaldehyde
E. Hypothesis and Explanation
1. Tollens Test
We make tollens reagent with add 2 ml of AgNO3 5% solution
(colorless) into test tube, then added 2 drops of 5% NaOH solution
(colorless). This reaction produced brown precipitate of Ag2S. The
reaction can write with :
2AgNO3 (aq) + 2 NaOH (aq) → Ag2O (s) ↓ + 2 NaNO3 (aq) + H2O(l)
(gray precipitate)
Next, added drop by drop of NH4OH 2% solution and shaked it
until the precipitate dissolve. This process produce tollens reagent. The
ammonia addition purpose to prevent the precipitation of silver ions as
oxides (Ag2O) at high temperatures. The reaction can write in :
Ag2O (s) + 4 NH4OH (aq) + 2 NaNO3 (aq) → 2 [Ag (NH3)2]NO3 (aq)
(tollens reagent) + 2NaOH (aq).
 1 ml of tollens reagent took into test tube to identify the organic
compound that contain aldehyde and ketones. Added 2 drops of
benzaldehyde, shaked it and let until 10 minute to form precipitate like
silver mirror in bottom of test tube that indicate that this compound
contain an aldehyde group. If there is no reaction, put it into hot water
(35-50oC) until 5 minute to help reaction happen with increase the
temperature. Benzaldehyde produce silver mirror that indicate that this
compound is a group of aldehyde.
1 ml of tollens reagent took into test tube and added 2 drops of
acetone compound to identify it like last procedure. No changes or the
solution is colorless. It means that tollens identify that this compound
not contain aldehyde group. The reaction of this can write with :
O O
+ +
H3C C 3+2
H3C CHC CH[Ag(NH 3)2] +3)H
3 + 2 [Ag(NH 2]2O+ H2O

Next, 1 ml of tollens reagent took into test tube and added 2 drops
of cyclohexanone compound to identify it like last procedure. The
solution was dark grey with 2 layers. Because when the
cyclohexanone compound is reacted with the tollens reagent, the
cyclohexanone compound can not reduce the tollene reagent, because
to reduce the ketone requires strong oxidation, whereas the tollene
reagent includes a weak oxidizer. It means that tollens identify that
this compound not contain aldehyde group. The reaction of this can
write with :
O

+ 2 [Ag(NH3)2]+ + H2O

In test tube 4 added 2 drops of colorless formalin. Then shaken and

allowed to stand for 10 minutes. After being shaken and allowed to
stand for 10 minutes the solution remains unchanged (colorless
solution).
 Then prepare a water bath. Place the four test tubes into a water
bath with a temperature of 35o-50oC for 5 minutes. Observation th
result. The principle of this Tollens test is used to distinguish aldehyde
and ketone compounds in a sample by adding Tollens reagents. The
reaction that occurs is the oxidation reaction and the reduction
reaction. The tollens reagent ie a silver-ammonium ion solution, is
reduced by aldehydes to silver metal, while the aldehydes are oxidized
to the corresponding acid. Positive test is characterized by the
formation of a silver mirror on the wall in the test tube. The ketone is
not oxidized by the tollene reagent as it is a weak oxidizer. With
reaction :
O O

H C H (aq) + 2Ag(NH ) OH (aq)  H

3 2
C ONH4 + 2Ag

(s) + 3NH3 (aq) + 2H2O (l)

2. Fehling Test
For the first tube, put 5 mL Fehling reagent then putting the tset
tube in boiling water (3-4 minute) and observe the change that occur
10-15 minutes and then tested on fromaldehyde.
The first tube which is containing Fehling reagent and
formaldehyde, berlin blue solution is appear and dissolved in. But after
heated, there are formed red precipitate. The reaction that occur is:
O O

H C H + 2Cu2+ + NaOH + H2O H C ONa + Cu2O + 4H+

Red

The bistartratocuprate(II) complex oxidizes the precipitate

aldehyde to a
carboxylate anion. And in the process the copper(II) ions of the
complex are reduced to copper(I) ions. Red copper(I) oxide then
precipitates out of the reaction mixture, which indicates a positive
result.
In the second test tube, 5 mL of newly created fehling reagent was
added and then three drops of formaldehyde were added as the
 substance to be tested, the solution will remain dark blue. Then it is
heated in a water bath and observed for 10-15 minutes. However, when
heated the acetone added with the fehling reagent will not change the
solution remain dark blue. This shows that the acetone which is a
ketone compound gives a negative result in the fehling reagent. The
reaction can write with :
CH3COCH3(aq) + 2Cu2+(aq) + 5 OH-(aq) → (no react)
(Svehla, 1979)
In the third test tube, testing of cyclohexanone. Same is the
case with aceton, cyclohexanone and 1 mL of the fehling reagent are
added to the test tube the solution remains dark blue in color. Then it is
heated in a water bath and observed for 10-15 minutes. And there will
no change, the solution remains dark blue. This indicates that
cyclohexanone which is a ketone compound gives negative results on
fehling reagents. Fehling reagents which act as weak oxidizing agents
cannot oxidize cyclohexanone so that they do not produce reactions.
The reaction of this can write with :

(aq) + + 2Cu2+(aq) + 5OH-(aq) → (no react)

(Svehla, 1979)
This means, Fehling reagent can be used to identify the aldehyde
functional group it will form characterized by red precipitate in the
solution after heated the mixture. Aldehydes are oxidized, giving a
positive result, but ketones do not react, unless they are alpha-hydroxy-
ketones.
3. Bisulfite Addition
This experiment has purpose to know the principle of addition in
aldehyde. The first, measuring 5 mL of saturated NaHSO3, then put into
erlenmeyer and chill the solution in cooled in room temperature and
noted the temperature. The function of adding saturated NaHSO3
solution is because it serves to break the double bond into a single bond
on acetone proven by the formation of white crystalline. Next step is
 added 2,5 ml acetone to act as a double bonding agent in the carbonyl
group, to be addition with saturated sodium bisulfate. Then let stand 5
minutes, to know the reaction happen or not. Next, added 10 mL of
ethanol (colorless). The function of adding ethanol is to serve as one of
the compound that will react to form a crystal. The condition of the
solution is exothermic, this can be known from a little heat in the test
tube. The equation of the reaction is:

4. (aq)

+ NaHSO3(aq) →

After that the result is filtered with filter funnel and filter paper.
The result is a white-colored residue on a filter paper and colorless
filtrate inside the test tube. To prove the theory then crystal added 3-5
drops of concentrated HCl (colorless) until crystal dissolved. The HCl
is added as a solvent of the crystal and to separate the carbonyl
compound. Then written the end result of a crystalline dissolved in
concentrated HCl. The equation of the reaction is:
OH
O
+
H3C C SO3Na HCl→
+
H3C C CH3 + NaCl + SO2 ↑ + H2O
CH3

5. Testing with Phenylhidrazin

This experiment is based on an addition reaction. In this
experiment phenylhydrazin causes these compounds to react to produce
phenylhidrazine after the initial reaction results freeing one molar. The
results of these reactions are often in the form of crystalline deposits, so
that they can be used (through their melting points) to identify aldehyde
and ketone compounds.
First, in tube 1 added 10 drops of benzaldehyde. Then the test tube
is closed and shaken 1-2 minutes until the results are mixed. This
experiment proves that benzaldehyde can react with phenylhydrazine
because the electron-free pair of phenylhydracin causes this compound
to react and produce phenildrazone. In tube 1, a yellowish-white
precipitate and a pungent odor were obtained. The existing crystal is
then filtered with filter paper and funnel. Then the residue is washed
with cold water. After that, add a little by little ethanol until there is
concentrated crystallization. The function of ethanol is to dissolve
phenylhidrazine. After adding to ethanol, the crystal or residue is stored
in a desiccator to dry the crystal. Storage in the desiccator to dry takes 1
day. After drying, the color of crystal which has dried from
benzaldehyde is orange. The melting point is determined by using a
melting block.
The second test with phenylhidrazin, carried out on cyclohexanone.
The first step is to measure 2.5 ml of phenylhidrazin (orange solution)
using a measuring cup. The next step, 2.5 ml of phenylhydracin that has
been measured is inserted into a test tube that has been labeled with
tube 2. Then 10 drops of cyclohexanone (colorless) are added. ) into the
test tube. Then the tube is closed and shaken vigorously for 1-2 minutes
so that the solution is homogeneous to produce crystal in the form of a
brownish-red precipitate at the top of the test tube, which indicates the
formation of phenylhydrone.
The next step is the solution filtered with a filter funnel and filter
paper. The results are poured slowly into the funnel that has been
placed filter paper on it. The result is a residue in the form of a brown
precipitate on filter paper and clear filtrate located in the test tube. Then
the crystal is washed with cold water. . You do this by dripping distilled
water with dropper drops into the sludge that is still located in the
funnel through the funnel wall slowly. These quades serve to strengthen
the shape of the sludge (forming a perfect crystalline deposit).
The next step is the sludge put into a test tube and added ethanol /
methanol (colorless) solution of 3-5 drops. This is done to ensure that
the sludge is free from contamination of other substances and to
increase the amount of sludge so that it is easily observed. Then the
sediment is allowed to dry.
Through Tests with phenylhydrazin, compounds which when
tested with phenylhydrazin produce orange deposits with high melting
points
6. Haloform Reaction
The haloform reaction test using iodine can also be called iodoform
test. Iodoform test is used to determine the ability of aldehydes and
ketones to be ionized. The requirement for a compound to be ionized
against the iodoform test is characterized by the formation of yellow
precipitate. The principle in this experiment was to show the presence
of methyl ketone by learning aldehydes and ketones which produced
haloform compositions when iodinated. The compounds purchased are
acetone and isopropyl alcohol.
This reaction has been used in qualitative analysis to indicate the
presence of a methyl ketone, R-CO-CH3. In this experiment
used 2 samples , namely acetone and isopropyl alcohol. Initially a 3 mL
sodium hydroxide solution of 5% is prepared. The solution
is a solution that is not colored. Then inserted into the
tube reaction 1. The function of the addition of NaOH is to provide an
atmosphere bases in solution, the compound trihalo that produced
this easy once described by bases generate haloform. By because it was,
the reaction it can be used to provide iodoform . Then, add 5 drops of
acetone. Acetone is a solution is not colored. Function acetone
is added as a basic ingredient in the production of iodoform and as a
connector for the methyl group CH3(COI)2 which functions as an
oxidizer. When added, the solution still not colored . Iodine solution
is added about 10 mL while being shaken until the color of iodine does
not disappear again. The function of the addition of
iodine is to establish haloform types of iodoform Iodine is a
solution that is colored brown reddish. Once added iodine solution into
a non -colored and are precipitated colored yellow and has a
characteristic odors. It is indicates that iodoform was formed perfectly.
O O

CH3 C CH3
(aq) + 3I2 (aq) + 3OH- (aq)  CH3 C CI3
(aq) +
3H2O (l) + 3I- (aq)
 O O

CH3 C CI3
(aq) + OH- (aq)  CH3 C O
(aq) + CHI3 (aq)
The results of the reaction will form yellow deposits and have a
characteristic odor
The NaOH function according to March and Smith (2007), is
because the halogenation reaction of methyl ketone occurs because of the
presence of a base, for which NaOH is added to present a base. According
to Fessenden and Fessenden (1986), and the residual NaOH causes
decomposition of iodoform when reacted with ethanol. The addition of I2
aims to replace hydrogen which is bound to alpha C atoms with halogen
compounds.
The methyl group from a methyl ketone is gradually iodinated until
a solid yellow iodoform (CHI3) is formed (Fessenden and Fessenden,
1986). Therefore, yellow deposits are iodoform deposits (CHI3)
indicating that true acetone is methyl ketone. The emergence of drug
odor also indicates that iodoform has been formed.
7. Aldol Condensation
The seventh experiment is aldol condensation. the aim of this
experiment was to identify aldehyde groups through aldol
condensation. the principle of this experiment is that the aldehyde
group will condense with each other after reacting with a dilute base
solution and produce aldol which when heated removes water to
produce unsaturated aldehydes, namely crotanaldehyde.
The first step is to put 4 ml of 1% NaOH into a test tube. then
added with 0.5 ml of acetaldehyde (a colorless and odorless solution).
the next step is shaken and heated in a water bath until it boils. after
heating the solution turns yellow and smells rancid. The solution is the
result of aldol condensation which is a cystonaldehyde compound
which also has a characteristic rancid odor. If acetaldehyde is reacted
with a dilute base solution, which is a 1% NaOH solution, it will
condense with each other to produce aldol, which when heated will
 remove water to produce unsaturated aldehydes. reaction that occurs as
follows :
O O

NaO
CH3 C H
(aq) + CH3 C H
(aq)
OH O

CH3 C CH2 C
H
H (aq)

Reaction Mechanism that occurs

O O
- -
OH
CH3 C H H 2C C H
O O O
-
CH3 + H 2C  CH3
C H C H C CH2 C H

CH3 C CH2 C H heat

-
O OH

H3C CH CH C H

crotonaldehyde

(Svehla, 1979)

From this aldol condensation experiment it can be concluded that

the aldehyde group can be identified through aldol condensation which
is marked by a rancid odor that is formed namely the odor of
crotonaldehyde