I.

TITLE OF EXPERIMENT : “Identifying of Aldehydes, Ketones, and

Carboxylic Groups”
II. DATE OF EXPERIMENT : Wednesday, 8th March 2017
III. TIME OF EXPERIMENT : 09.00 – 14.40 WIB
IV. GOAL OF EXPERIMENT :
1. Identify organic compound contain with aldehydes group.
2. Identify organic compound contain with ketones group.
3. Identify organic compound contain with carboxylic group.
4. Understanding the difference between aldehyde, ketone, and carboxylic
compound.
V. BASIC THEORY
The simplest carbonyl compounds are ketones and aldehydes. A ketone
has two alkyl (or aryl) groups bonded to the carbonyl carbon atom. An aldehyde
has one alkyl (or aryl) group and one hydrogen atom bonded to the carbonyl
carbon atom.

R R' R H
C C C

O O O

ketone aldehyde carbonyl

group
condensed structure: RCOR’ RCHO (Wade, 2006:805)
Ketones and aldehydes are similar in structure, and they have similar properties.
They are some differences, however, particularly in their reaction with oxidizing
agents and with nucleophiles. (Wade, 2006:806)
The combination of a carbonyl group and a hydroxyl on the same carbon
atom is called a carboxylic group. Compounds containing the carboxyl group are
distinctly acidic and are called carboxylic acids.
H O R O
C H C H

O O R-COOH R-
CO2H
carboxyl group carboxylic acid condensed
strutures (Wade, 2006:935)
Carboxylic acid are similar in some respects to both ketones and alcohols. Like
ketones, the carboxyl carbon is sp2-hybridized, and carboxylic acid groups are
therefore planar with C-C=O and O=C-O bond angels of approximately 120o.
(McMurry, 2007:605)
Silver ion, Ag+, oxidizes aldehydes selectively in a convenient functional-
group test for aldehydes. The Tollens test involves adding a solution of silver-
ammonia complex (the tollens reagent) to the unkwon compound. If an aldehyde
is present, its oxidation reduces silver ion to metallic silver in the form of a black
suspension or a silver mirror deposited on the inside of the container. Simple
hydrocarbons, ethers, ketones, and even alcohols do not react with the tollens
reagent. (Wade, 2006:852)

Tollens Reagent Silver Mirror

(Tim dosen kimia organik, 2017:2 )
Benedicts test: measured proportions of sodium citrate and sodium
carbonate are dissolved in water. In this solution, copper sulphate is dissolved.
The resulting solution is called benedict reagent. Addition of benedict reagent to
glucose or fructose solution followed by heating in water bath result in the
formation of a red precipitate, due to the formation of cuprous oxide. (Reduction
of Cu2+ to Cu1+)
Fehling reagent is an alkaline solution of cupric ion complexed with
sodium or potassium tartarate ions. When this reagent is added to glucose or
fructose solution followed by heating in water bath result in the formation of a
red precipitate. This is due to the reduction of Cu2+ to Cu1+. (Trishna, 2009:367)

Red Precipitate
(Tim dosen kimia organik, 2017:2)
Common reaction of carbonyl compounds is an addition reaction to bond
Duplicate carbonyl. Usually a nucleophilic reagent. Aklehid and some ketones
which do not contain large groups around the carbon atom of the carbonyl reacts
with a concentrated solution of sodium bisulfite adduct yield tangible white
crystal. This adduct when react with acids frees back carbonyl compound, so the
reaction is sometimes useful to separating carbonyl compounds from mixtures
with other compounds. (Tim dosen kimia organik, 2017:2-3)
 The lone pair on the nitrogen atom of ammonia and compounds other
similar causes these compounds may react to produce phenyl hydrazone after
reaction products initially form liberate one mole water. These results are often
intangible crystal, so that it can be used (through point melting) to recognize
aldehydes and ketones. The same reaction with 2,4-dinitro produce 2,4-dinitro
phenylhydrazine fenilhidrazon which usually has a point higher melting.

Hydroxyl amine when it reacts with carbonyl compounds to produce

oxime, which can also be used for the introduction. In addition, the oxime is used
anyway as intermediates in the synthesis, for example, heating in alkaline
conditions produce hydrocarbons comparable.

The hydrogen atoms attached to the carbon atom adjacent to the carbonyl carbon
atom called the alpha carbon atom, is weakly acidic. This is because the charge
of the anion in question (enolate anion) may be submitted to the oxygen atom
electronegative. (Tim dosen kimia organik, 2017:3)

(Tim dosen kimia organik, 2017:4)

 It is an oxidation reaction which is specific for methyil ketones. It
consists in reacting the methyl ketone with sodium hypohalite (an alkaline
solution of halogen). The ketone is oxidised to an acid having one carbon atom
less than the parent ketone and haloform (CHX3) is formed simultaneously.
If the hypohalite used in this reaction is sodium hypoidite, the product is
iodoform (CHI3). Such a haloform reaction is also known as the iodoform test.
As iodoform is a yellow srystalline solid with a characteristic odour and melting
point,it can be handled much more easily in a laboratory, iodoform test is
paraticulary useful as diagnostic test for methyl ketones. (Raj, 2008:188)

(Tim dosen kimia organik, 2017:4)

VI. Equipment and Materials
Equipment
- Test tube 4 pcs
- Thermometer 2 pcs
- Erlenmeyer 50 mL 2 pcs
- Funnel Hirsch 1 pcs
- Funnel Buchner 1 pcs
- Filter paper + filter flask (as needed)
- Beaker glass 100 mL 2 pcs
- Spirtus burner + kasa 1 pcs
- Pipette (as needed)
- Measuring glass 10 mL (2 pcs)
- Arloji glass (2 pcs)
- Refluks cooler (1 pcs)
- Capillary tube (2 pcs)
- Conical flask (4 pcs)

Materials
- AgNO3 5 % solution 2 mL
- NaOH 5 % solution 2 drops
- NaOH 10 % solution 12 mL
- NH4OH 2% solution 4 mL
- Benzaldehid 2 mL
- Aseton 2 mL
- Cyclohexanon 10 drops
- Formalin 1 mL
- Etanol 10 mL
- 2-pentanon 10 drops
- N-heptaldehyde 10 drops
- Fehlingt reagent 20 mL
- Sodium bisulphide concentrated solution
- Phenilhydrazine reagent 10 mL
 - Ice as needed
- HCl 3M 2 mL
- Isopropyl alcohol 1 mL
- Asetaldehyde 0,5 mL
- CH3COONa solution 10% 1 mL
- KMnO4 1N 1 mL
- FeCl3 solution 5% 3 mL
- K4FeCN6 1M 2 mL
- H2SO4 concentrate 1 mL

VII. WORK OF FLOW

A. Testing Tollens
Making Tollens Reagent
2 mL Larutan AgNO3 5%

- Pouring into test tube that has been washed with

soap+water and dried
- Adding 2 drops of NaOH solution 5%

Brown Precipitate

- Adding NH4OH Solution 2% drop by drop and

shaking it until dissolve

Tollens reagent

1 ml tollens reagent

- Pouring into test tube A, B, C, D

- Adding 2 drops benzaldyde in test tube A,
2 drops acetone in test tube B, 2 drops
cyclohexanone in test tube C, and 2 drops
formaline in test tube D
- Shaking It
- Waiting for 10 minutes
- Boiling (35°-50°C) for 5 minutes
- Observing the test tube

Brown Precipitate
B. Testing Fehling And Benedict

Making fehling Reagent

10 ml fehling A

- Pouring into beaker glass

- Adding 10 ml fehling B
- Stirring it

Fehling Reagent

5 ml fehling reagent

- Pouring into test tube 1, 3, 4

- Adding Few Drop Of Formaldehyde in test tube
1, Few Drop Of Acetone in test tube 3 and few
drops of cyclohexanone in test tube 4
- Putting test tube 1, 3, 4 into boiling water
- Observing after 10-15 minutes

Sorrel precipitate in test tube 1,

not reacted in test tube 3 and 4

Nb : Testing fehling didn’t conduct in test tube 2 because there is no n-

heptaldehyde
 C. Bisufite Addition

5 ml NaHSO3 saturated solution

- Pouring into erlenmeyer 50 ml

- Cooling into ice water
- Adding 2.5 ml acetone drop by drop and shaking
(until crystal is formed)
- After 5 minutes, adding 10 mL ethanol
- Filtering with filtered funnel

Residue (white crystal) Filtrate

- Adding few drop of concentrated

Hydrochloric acid
- Observing
- Writing the result

Observing Result

D. Testing With Phenylhydrazine

5 ml Phenylhydrazine

- Pouring into test tube 1, 2

- Adding 10 drops benzaldehyde into test tube 1, 10
drops cyclohexanone into test tube 2
- Shaking with covered the tes tube’s nozzle For
about 1-2 minutes (until the crystal is formed)
- Filtering with filtered funnel

Residue (crystal) Filtrate

- Watering with few cold water

- Adding few methanol or ethanol
- Drying it in desicator
- Determining the melting point

Melting point
E. Haloform Reaction

3 mL of 5% Sodium Hydroxide
solution solution 5%
- Pouring into test tube 1 and 2
- Adding 5 drops of aseton in test tube 1 and 5 drops
of isopropyl alcohol in test tube 2
- Adding 10 mL iodium solution
- Shaking until the colour of iodium isn’t lost
- Observing the test tube
- Smelling it

Yellow sediment &

has an odor

F. Condensation of Aldol

4 mL of 1 % Sodium Hydroxide solution

1%
- Pouring into test tube
- Adding 0,5 mL asetaldehyde solution
- Shaking
- Smelling it
- Boiling until 3 minutes
- Observing
- Smelling it again

Has an odor
(smell krotonaldehide)
Refluks Method

5 mL Sodium Hydroxide 5% + 1 mL aseton

+ 2 mL benzaldehide + 10 mL etanol

- Pouring into boiling flask flat bottom 50

mL that is connected with condensor
- Refluxing for 5 minutes
- Cooling
- Filtering with Buchner filter

Filtrate
Residue

- Can be crystalized again from ethanol

- Observing
- Determining the melting point

Melting Point

G. Identification of Carboxilic

5 mL Acetic Acid

- Pouring into test tube

- Adding 3 mL of KMnO4 solution
- Observing

Observing Result
 5 mL Sodium Asetate solution 10%

- Pouring into test tube

- Adding 3 mL FeCl3 5% solution until the colour change into red
- Heating the test tube until the precipitate color is brownish red
- Filtering with the funnel

Residue
Filtrate

- Adding K4FeCN6 to prove that there isn’t ferri ion

- Observing
- Comparing the colour of observation with the
colour of ferri chloride with the same amount

Observing Result
(Colour Change)
 VIII. OBSERVATION RESULT

No Procedure Experiment Result Reaction Conclusion

Before After
A. Testing Tollens  AgNO3 solution 5 % :  AgNO3 + NaOH : - Based on the theory
colorless brown precipitate aldehide group must
 NaOH solution 5 % :  Brown precipitate + 2AgNO3(aq) +2NaOH(aq) be form silver
2 mL Larutan colorless\ NH4OH :  Ag2O(s) + NaNO3(aq) mirror. But the
AgNO3 5%  NH4OH solution 2 % : colorless(but view + H2O(aq) higher temperature
colorless precipitate) (more than 500C)
- Pouring into test tube that has causing silver
mirror didn’t form.
been washed with
soap+water and dried - Ketone group
- Adding 2 drops of NaOH (acetone and
solution 5% cyclohexanone) can
not react with
Brown tollens reagent.
Precipitate

- Adding NH4OH Solution 2%

drop by drop and shaking it
until dissolve

Tollens
reagent
 Test tube A :
1 ml tollens reagent  Benzaldehyde :  Tollens reagent +
colorless benzaldehyde :
- Pouring into test tube A,  Acetone : colorless turbid
 Cyclohexanone : - Heating : turbid
B, C, D colorless (silver mirror
- Adding 2 drops  Formaldehyde : not form)
benzaldyde in test tube colorless  Tollens reagent +
acetone : hablur (+)
A, 2 drops acetone in test
- Heating : hablur
tube B, 2 drops (++)
cyclohexanone in test  Tollens reagent + Test tube B:
tube C, and 2 drops formaldehyde : grey
precipitate
formaline in test tube D
 Tollens reagent +
- Shaking It cyclohexanone :
- Waiting for 10 minutes turbid
 After tollens Test tube C:
- Boiling (35°-50°C) for 5
reagent +
minutes formaldehyde was
- Observing the test tube heated = grey
 After tollens
Brown Precipitate reagent Test tube D :
+cyclohexanone
was heated = dark CH2O +
grey
2Ag(NH3)2OH(aq)
B. Testing Fehling  Fehling A : Light  Fehling A + - Formaldehyde
Blue fehling B : dark 2KNaC4H4O6 + 2Cu2+ + can react with
10 ml fehling A
 Fehling B : blue 2OH- fehling reagent
colorless Test tube I Cu[C4H4O6]22- + form sorrel
- Pouring into beaker glass  Formaldehyde :  Fehling reagent Cu(OH)2 + precipitate
- Adding 10 ml fehling B colorless + formaldehyde : 2Na+ + 2K+ + 2N+ - Acetone and
- Stirring it  Asetone : colorless dark blue cyclohexanone
 Cyclohexanone :  Fehling reagent ketone) can not
Fehling Reagent + formaldehyde Test tube I react with fehling
colorless
+ boiling : dark CH2O + 2Cu2+(aq) + reagent
-
5 ml fehling reagent blue solution 5OH 
with sorrel CHO2 + Cu2O+ 3H2O
precipitate
- Pouring into test tube I,
Test tube III
III, IV
 Fehling reagent Test tube III
- Adding Few Drop Of
+ acetone : dark C3H6O (aq) + 2Cu2+
Formaldehyde in test blue
tube I, Few Drop Of  Fehling reagent (aq) +4OH-(aq)
Acetone in test tube III + acetone +
and few drops of boiling : dark
cyclohexanone in test blue Test tube IV
tube IV Test tube IV
- Putting test tube I, III,  Fehling reagent
IV into boiling water + cyclohexanone
- Observing after 10-15 : dark blue
minutes  Fehling reagent
Sorrel precipitate in test tube I, not + cyclohexanone
reacted in test tube III and IV + boiling : dark
 blue solution

C. Bisulfite Addition  NaHSO3 (aq) :  NaHSO3 - Acetone (ketone)

colorless saturated was can react with
5 mLof NaHSO3 saturated
 Acetone : added 2,5 mL NaHSO3 form a
colorless acetone drop by hablur that
- Pouring into conical flask 50
 Ethanol : colorless drop and become colorless
mL  HCl concentrate : shaking, produce again after adding
colorless colorless HCl concentrate.
- Cooling into ice water
solution
- Adding 2,5 mL acetone drop  And then 5
by drop while shaking minutes later,
solution was
- After 5 minutes, adding 10
added by 10 mL
mL ethanol (until crystal is ethanol, the
formed) solution become
white hablur
- Filtering with filtered funnel
 Hablur + HCl
Residue Filtrate concentrate :
- Adding few drop of
hablur dissolve
and the color of
concentrated HCl
solution is
- Observing
colorless.
- Writing the result

Hablur dissolve and colorless

solution
D. Testing with phenylhydrazine  Phenylhydrazine :  Test tube I Reaction between
yellowish Phenylhydrazine + phenylhydrazine and
5 mLof phenylhydrazine  Benzaldehyde : benzaldehyde : benzaldehyde, the
colorless white solution melting point of
- Pouring into test tube I, II  Cold water : After the test tube benzaldehyde is 1200C
colorless was shaken, in the
- Adding 10 mL of benzaldehyde
 Ethanol : colorless solution there are
into test tube I, and 10 drops of  Cyclohexanone : yellow crystal Reaction between
colorless phenylhydrazine and
cyclohexanone into test tube II
 Test tube II cyclohexanol, the
- Shaking with covered the test Phenylhydrazine + melting point of
tube’s nozzles for 1-2 minutes cyclohexanone : cyclohexanol is 820C
turbid solution
(until the crystal is formed)
After the test tube
- Filtering with filtered funnel was shaken, in the
solution there are
Filtrate yellow crystal
Residue

- Watering with few cold water

- Adding few methanol or ethanol
- Drying
- Determining the melting point

Observation result
E. Haloform Reaction NaOH : colorless Test tube 1 Isoprophyl alcohol and
Acetone : colorless  NaOH acetone can produce
Isoprophyl alcohol : solution + 5 haloform. It also has an
3 mL of 5% Sodium colorless drops of odor
Hydroxide solution I2 solution : reddish acetone :
-solution
Pouring5%into test tube 1 brown (odor) colorless
and 2  NaOH
- Adding 5 drops of solution + 5
acetone in test tube 1 drops of
and 5 drops of isopropyl acetone + I2
alcohol in test tube 2 solution :
- Adding 10 mL iodium yellow
sediment and
solution
has an odor
- Shaking until the colour
of iodium isn’t lost Test tube 2
- Observing the test tube  NaOH
- Smelling it solution + 5
drops of
Yellow sediment & isoprophyl
alcohol :
has an odor colorless
 NaOH
solution + 5
drops of
isoprophyl
alcohol + I2
 solution :
yellow
sediment and
has an odor

F. Condensation of Aldol  NaOH : colorless  NaOH + Aldehyde can produce

 Asetaldehyde : asetaldehyde + aldol with
4 mL of 1 % Sodium colorless shaking = krotonaldehyde odor.
Hydroxide solution 1% yellow
- Pouring into test tube solution and
- Adding 0,5 mL has an odor
asetaldehyde solution  NaOH +
- Shaking asetaldehyde +
boiling =
- Smelling it
orange
- Boiling until 3 minutes solution and
- Observing has a stronger
- Smelling it again odor (krotonal
dehyde)
Has an odor

(smell krotonaldehide)
Refluks Methode
5 mL Sodium Hydroxide 5% + 1 mL
aseton + 2 mL benzaldehide + 10 mL
etanol
- Pouring into boiling
flask flat bottom 50 mL
that is connected with
condensor
- Refluxing for 5 minutes
- Cooling
- Filtering with Buchner
filter

Residue Filtrate

- Can be crystalized again from

ethanol
- Observing
- Determining the melting point
Observation result
G. Identification of Carboxilic Acetic acd : colorless Acetic acid + CH3COOH(aq) + 2MnO4-  Carboxylic acid
KMnO4 : purple KMnO4 : purple 3CO2(g) + 2MnO4(s) + 2OH- oxidized by KMnO4. In
5 mL Acetic Acid
Sodium acetate : + 2H2O(l) the filtrated there is no
colorless ferri ion that can proven
- Pouring into test tube FeCl3 : yellow CH3COONa(aq) + FeCl3(aq) + with K4FeCN6
- Adding 3 mL of KMnO4 K4FeCN6 : yellow H2O(l) 
Fe(OH)2(CH3COOH)(s) +
solution
CH3COOH + 3NaCl
- Observing
Fe3+(aq) + 6CN-(aq)
Observing [Fe(CN)6]3-(aq)
Result

5 mL Sodium Acetate solurion

10% Sodium acetate +
FeCl3 : red
- Pouring into test tube Sodium acetate +
FeCl3 + heating :
- Adding 3 mL FeCl3 5%
brownish red
solution until the color Filtrate : colorless
change into red Filtrate + K4FeCN6 :
- Heating it until there is yellowish green
brownish reds lump
precipitate FeCl3 : Filtrate +
- Filtering K4FeCN6
Yellow : Yellowish
-
green
 Filtrate Residue

- Adding K4FeCN6 to prove

that there isn’t ferri ion
- Observing
- Comparing the color of it
with ferri chloride with the
same amount

Observation result
IX. ANALYSIS
In this experiment about “Aldehyde and Ketones” that purposed to learn
the principles of the reaction of carbonyl compounds, understanding the
reaction experiments between aldehydes and ketones, and proving type of
simple chemical test that can distinguish aldehydes and ketones. There are six
experiments that we have done to identify them, the step will be explain as
follow :
A. Tollens Reagent Testing
The purpose of this experiment is to distinguish aldehyde and ketone
group based addition of Tollens reagent. The first step in this experiment is
making of tollens reagent. 2 mL of AgNO3 5% solution (colorless) is poured
into test tube that has been washed with soap and water and dried in oven.
The equipments (test tubes and pipettes) have to wash before, so the
equipments are clean from pollutant compounds because tollens reagent is
very sensitive and it can affect the experiment result (the silver mirror is not
formed). Then, the solution is added 2 drops of NaOH 5% solution
(colorless). The reaction can be written:

2AgNO3 (aq) + 2NaOH (aq)  Ag2O (s)  + 2NaN3 (aq) + H2O (aq)

From the reaction, we know that the reaction of solution produces dark
gray precipitate. The precipitate is Ag2O. AgNO3 solution 5% will oxidize the
sample and form silver mirror cause Ag+ ion that reduced become silver.
After that, the precipitate is added NH4OH solution 2% (solution) drop
by drop. The compound is shaken while NH4OH solution 2% still added until
the precipitate dissolved and produces tollens reagent. The solution is more
clear than before. 2% NH4OH solution is used to prevent Ag+ ion precipitate
as oxidizing agent of AgNO3 in high temperature. It makes the sample in
base condition as well. The reaction can be written:

AgNO3 (s) + NH4OH (aq)  2Ag(NH3)2+ + 3OH-

The results of the reaction is known as a reagent tollens that containing

silver-ammonia (Ag(NH3)2+). The function of Tollens reagent is to identify
the presence of aldehydes group in a compound. It is proven by formation of
silver precipitate (Ag), like silver mirror on the tube of solution that contains
aldehydes group.

The next step, we prepared four test tubes that has been washed with soap
and water and dried in oven. Than, the test tube was given label I, II, III, and
IV. 1 mL of tollens reagent was added into each of test tube. After that, 2
drops of benzaldehyde (colorless) was added into test tube I, 2 drops of
acetone (colorless) into test rube II, 2 drops of cyclohexanone (colorless) into
test tube III, and 2 drops of formaline (colorless) into test tube IV. Formaline
solution was made from 5 drops of formaldehyde is diluted in 5 mL of water.
Then, each of test tube was shaken. All of solution in test tube was allowed
for 10 minutes and there is have not a changing. After that, the samples is
heated. The water in beaker glass was heated. After that all of test tube is
entered into beaker glass and boiled for 5 minutes at 300C - 500C and than it
is observed. This is the result of observation:

 Benzaldehyde

The first compound that tested by Tollens reagent is benzaldehyde.

Initially the color of Tollens reagent is colorless. When Tollens reagent is
reacted with benzaldehyde (after heating process), the color of solution
become light yellow and there are any granule. The hot water as an
accelerator reaction with the Tollens reagent and benzaldehyde.
The reaction can be written:

O
+ 2Ag(NH3)2OH  + 2Ag + 2NH3+
CH

From the reaction, we know that should produce silver mirror. But
O
after the compound is heated, there is no silver mirror is formed. This is
COH
an indication, the mistake happened in experiment.
 Acetone
The second compound that tested by Tollens reagent is acetone. Initially the color
of Tollens reagent is colorless. When Tollens reagent is added acetone and is heated,
the color of compound become light yellow. The reaction can be written:

CH3COCH3(aq) + 2Ag(NH3)2OH(aq)

When Tollens reagent is reacted with acetone, there’s no changing occurs although
the solution is heated. From the reaction we know, the reaction can not happen. It is
because ketones only can be being oxidation in the hard condition of reaction, than
aldehydes is more reactive than ketones. So, ketones group can not react with Tollens
reagent.

 Cyclohexanone
The third compound that tested by Tollens reagent is cyclohexanone. Initially the
color of Tollens reagent is colorless and the color of cyclohexanone is yellow.When
Tollens reagent is added cyclohexanone and is heated, the color of compound become
dark gray and black precipitate formed. The reaction can be written:

+ Ag(NH3)2OH (aq)

O
From the reaction we know, the reaction can not happen. It is because ketones only
can be being oxidation in the hard condition of reaction, than aldehydes is more
reactive than ketones. So, ketones group can not react with Tollens reagent.

 Formalyne
The fourth compound that tested by Tollens reagent is formalyne (colorless).
Initially the color of Tollens reagent is colorless. When Tollens reagent is reacted with
formalyne (after heating process), the color of compound become gray and black
precipitate formed.
 The reaction can be written:
O

H C
H (aq) + 2Ag(NH3)2OH (aq)
O

H C
ONH4 (aq) + 2Ag (s) + 2NH +(aq) + 2H O(l)
3 2

From the reaction, we know that should produce silver mirror. But after the
compound is heated, there is no silver mirror is formed. This is an indication, the
mistake happened in experiment

B. Testing Fehling
The second experiment in the trial of aldehydes and ketones is Testing Fehling. The
purpose of the test using Fehling reagent is to distinguish the intermediate aldehydes and
ketones. Principle Fehling test is oxidation and reduction reactions. Fehling testing will
give positive results in the aldehyde compound formation of deposits of sorrel
precipitate and a negative result in ketones.
First, put 10 ml of Fehling's A solution that have blue color is a solution of CuSO4
pouring into test tube and then adding 10 ml of Fehling's solution B is a solution of
NaOH colorless into test tube too. From the results obtained reagent mixing Fehling is
colored dark blue because it contains Cu2+ ions. The reaction is :

Against the Fehling reagent that has been made, 5 mL of fehling reagent is poured
into three different test tube, then added 4 drops of material to be examined, ie
formaldehyde, acetone, and cyclohexanone.
a. formaldehyde
After formaldehyde and Fehling reagent is added to a test tube solution remains colored
dark blue. Then heated in boiling water and observed for 5-10 minutes. But when heated
benzaldehyde are added Fehling reagent, dark blue solution began to show a sorrel
precipitate. This matter indicates that the benzaldehyde which is an aldehyde compound
provides positive results in Fehling reagent by means oxidized by reagents fehling.dan
formaldehyde reducing reagent Fehling. The reaction equation:
b. Acetone
A second test tube of the test using acetone. After acetone and reagents Fehling's
solution was added to the test tube remains colored dark blue. Then heated in boiling
water and observed for 5-10 minutes. However when heated acetone added Fehling
reagent solution remains unchanged colored dark blue. This indicates that the acetone
which is a compound ketone gives a negative result in reagent Fehling. Fehling reagent
which acts as a weak oxidizer that can not oxidize acetone not produce a reaction. The
reaction equation:

c. Cyclohexanone
The third test of the test is by using cyclohexanone. As well as with acetone.
After cyclohexanone and Fehling reagents added to test tube solution remains colored
dark blue. Then heated in water boil and observed for 5-10 minutes. However, when
heated cyclohexanone which added reagent solution remains unchanged Fehling colored
dark blue. This indicates that the cyclohexanone which is ketones leave a negative result
in reagent Fehling. Fehling reagent which acts as an oxidant weak can not oxidize
cyclohexanone so it does not produce a reaction. The reaction equation:
C. Bisulfite Addition
The next experiment is bisulfite addition. The principle of this experiment is
addition reaction in ketone. In this experiment use bisulfite compound to separate
aldehyde with the blend. To do this experiment, firstly preapare 5 mL of NaHSO 3
saturated solution that is colorless and pour it into conical flask 50 mL. After that,
cooling conical flask by entered it into beaker glass that contain with ice water. The
purpose of this step is to decrease the temperature so in this addtion reaction the
solution can produce hablur. After cooling, the solution added with 2,5 mL aceton that
is colorless drop by drop and shake it so the solution can evenly mixed. The solution is
still colorless.
The reaction is:
CH3 CH3
CH3
C C
H3C O + Na +
+ -
HSO3 
HO OSO2-Na2+

Then, wait until 5 minutes and add 10 mL of ethanol. The function of ethanol
in this experiment is to increase production of crystal so, the solution produce hablur
(white). The solution with white hablur filtered with funnel and filter paper produce
filtrate and residue. The residue is colorless solution and the filtrate is white hablur.
The white hablur moved using spatula into test tube and added few drops of HCl
concentrated that is colorless. The white hablur is dissolve become colorless solution.
It happen because adding HCl can make acid condition in the solution, so in acid
condition hablur (produce of addition bisulfite) become ketone again.
The reaction is:
CH3 CH3
CH3 CH3
C C
OSO -Na2+ OSO2-Na2+
HO 2 HO
↔
C2H5OH
D. Testing with Phenyl-hydrazine
The fourth experiment is testing use phenyl-hydrazine. The function of phenyl
hydrazine is to distinguish aldehydes and ketones group from their melting point. Phenyl
hydrazine is yellow solution and will form a precipitate when reacted with aldehydes and
ketones.
The first step in this experiment is, prepare two test tubes and labeling the test tube I
and II. Into both of test tube, 2.5 mL of phenyl-Hydrazine solution is poured. After that, 10
drops of benzaldehyde is poured into test tube I and 10 drops of cyclohexanone is poured
into test tube II. Next, the solution in test tube is shaken with covered for 2 minutes. Then,
the precipitate that produced is filtered. The filtering result produces recidu and filtrate. The
filtrate or precipitate is washed use few of cold water and re-precipitate again with ethanol.
After that, the precipitate is moved in the pantry dish and is put into desicator. The
precipitate is waited until the sample is dry. We wait for two days. Then, we can determine
the melting point of two compounds or samples.

 Melting Point Measuring of Benzaldehyde

The first compound that will be tested is benzaldehyde. After benzaldehyde which
is bright yellow solution is reacted with phenyl hydrazine, the solution becomes white
turbid solution and there are any yellowish orange precipitate are formed. In this
reaction, phenyl- hydrazone. The reaction can be written:
NH2
HN
H

O C N NH
H
(aq) + (aq)  (s)

+ H2O (l)
After we washed the precipitate with cold water and ethanol, we put it into
desicator and give label as sample I. After 2 days, we determine the melting point.
Firstly, the sample I is taken from desicator and prepared 1 set equipments that needed
to measure melting point. There are stative, clamp, block metal, thermometer, capillary
pipe, water bath, and spiritus. The capillary pipe is burned one of the end until clogged.
The sample is entered into capillary pipe more less 1 cm. The sample is placed in the
end of capillary pipe that is clogged.
 Then, equipments is assigned to measure the melting point and capillary pipe is
entered in the small hole of block metal while the thermometer is entered in the big hole
of block metal. Placing of thermometer does not touch until bottom so the temperature
can measure well. The water bath is turned on. The sample in capillary pipe is observed
until melt and written the temperature at the time it's melt.
The melting point of this compound (sample I) is 120oC. It shows this compound
has aldehydes group. Based on theory the melting point of benzaldehyde is 120oC. It is
appropriate with our result of melting point that we get. If it is compared with ketones,
its melting point is higher. It is because in aldehydes compound, there is hydrogen
bonding between molecules and make the bonding is stronger, so the melting point is
higher.

 Melting Point Measuring of Cyclohexanone

The second compound that will be tested is cyclohexanone. After cyclohexanone
which is colorless solution is reacted with phenyl hydrazine, the solution becomes
white turbid solution and there are any yellowish orange precipitate are formed. In this
reaction, phenylhydrazon is produced. After this compound is dried, the color of
precipitate become dark red . The reaction can be written:
H
O NH 2
N
N N

H
+  + H2O (l)

After we washed the precipitate with cold water and ethanol, we put it into
desicator and give label as sample II. After 2 days, we determine the melting point.
The steps is same with melting point measuring before. Firstly, the sample II is taken
from desicator and prepared 1 set equipments that needed to measure melting point.
There are stative, clamp, block metal, thermometer, capillary pipe, water bath, and
spiritus. The capillary pipe is burned one of the end until clogged. The sample is
entered into capillary pipe more less 1 cm. The sample is placed in the end of capillary
pipe that is clogged. Than, equipments is assigned to measure the melting point and
capillary pipe is entered in the small hole of block metal while the thermometer is
entered in the big hole of block metal. Placing of thermometer does not touch until
bottom so the temperature can measure well. The water bath is turned on. The sample
in capillary pipe is observed until melt and written the temperature at the time it's melt.
 The melting point of this compound (sample II) is 82oC. It shows this compound
has ketones group. Based on theory the melting point of cyclohexanone is 80oC. It is
different with our result of melting point that we get. It caused by the temperature in
the room are not constant. If it is compared with aldehydes, its melting point is lower.
It is because in ketones compound, there is no hydrogen bonding between molecules
and make the bonding is weaker, so that the melting point is lower.

E. Haloform Reaction
The next experiment is haloform reaction. Haloform reaction is to distinguish
aldehyde compound and ketone compound based on the ability to produce haloform
compound that contain with trihaloform in the form of iodoform in base condition.
Properly, in this experiment use 4 (four) different compounds that is aceton, isopropil
alcohol, 2-pentanone and 3-pentanone, but in the laboratorium just provide 2 (two)
compounds that aceton and isopropil alcohol.
First, preapare 3 mL of sodium hydroxide (NaOH) 5% solution that is
colorless and pour into test tube 1 and 2 in the same volume. NaOH as breaker of
methyl group that bond with carbonyl atom become trihalomethyl compound. Test tube
1 added with 5 drops of aceton that is colorlessand test tube 2 added with isopropil
alcohol that is colorles. The solution in test tube 1 and 2 is still colorless. After that,
adding 10 mL of Iodium solution (that have redish brown color and sting odor) into
test tube 1 and 2 and the solution have yellow precipitate and the smell is like drug.
Then, shake it until the color of iodium isn’t lost. The yellow precipitate is iodoform
that have smell is like drug.
The reaction is:
X. DISCUSSION
1. Tollens Reagent Testing
In the first experiment, it is testing of Tollens Reagent, the mistake
happened in test tube I and test tube IV. In test tube is reaction between
Tollens reagent and benzaldehyde while in the test tube II is reaction
between Tollens reagent and formalyne. Benzaldehyde and formalyne are
derivate of aldehyde compound.
Based on theory, if Tollens reagent is reacted with aldehyde
compound, it form silver mirror. It means that aldehydes can be being
oxidation become carboxylic acid salt. Tollens reagent can change C-H
bonding in aldehydes become C-O bonding and carbonyl group can
reduce Tollens (Ag(NH3)2OH) become Ag metal which forms as silver
mirror. The reaction is :

The Tollens Reagent is very sensitive with pollutant compound. The factor
caused fail the siver mirror forming, probably because the equipments that
used isn't really clean. The next factor is the temperature when heat the all
of sample is very high even more than rule. In this procedure should
temperature at 350C up to 500C. But the temperature that we used is 800C up
to 900C. This incident destroy the process of oxidation and reduction
reactions so can't form siver mirror.
XI. ANSWER OF QUESTION
1. Explaining the distinguisher to test qualitatively between compound which has
aldehyde, ketone, and carboxylic group!
Answer :
 Aldehyde Compound
Aldehyde compound can be tested use Tollens reagent. When aldehyde
compounds are reacted with Tollens reagent, it will produce silver mirror. Because
Tollens reagent can change C-H bonding in aldehydes become C-O bonding and
carbonyl group can reduce Tollens (Ag(NH3)2OH) become Ag metal which forms as
silver mirror. The reaction can be written:

 Ketone Compound
Ketone compound can be identified with oxidation process. In oxidation process
will happen of losing carbon-carbon bond produce two carboxylic acids. Each of
compound contain carbon atom that the amount is less from ketone first. The
reaction can be written:

 Carboxylic Compound
Carboxylic compound can be tested with esterification reaction. If carboxylic
compounds are reacted with alcohol compound use acid as catalysator, it will
produce esther with smell fragrance. The reaction can be written:
RCOOH + R'OH → RCOOR' + H2O
Carboxylic acid alcohol esther water
 2. Explaining the step to test distinguisher of function group between aldehyde and
ketone group use Fehling or Benedict testing!
Answer :
To test distinguisher of function group between aldehyde and ketone group use
Fehling or Benedict reagent, it can be identified of the reaction. When aldehyde
compound is reacted fehling or benedict reagent, it will produce sorrel precipitate. The
reaction can be written:

While, ketone compound can not react with fehling or benedict reagent. Fehling and
benedict has a complex ion Cu2+ in acid solution. Cu2+ ion is weak oxidator, so this ions
only can oxidate aldehydes, and can not oxidate the katones, like Tollens reagent.
Aldehyde compound + fehling reagent → sorrel precipitate
Ketone compound + fehling reagent → no reaction
 REFERENCES

McMurry, John.2007.Organic Chemistry.New York:Visil Thomson Book.

Raj, Gurdeep.2008.Organic Name Reaction, Reagents and Molecular
Rearrangements.India:S.K. Rastogi for KRISHNA Prakashan Media.
Tim Dosen Kimia Organik.2017. Buku Petunjuk Praktikum Kimia Organik. Surabaya :
Universitas Negeri Surabaya
Trishna.2009.CHEMISTRY.India:Dorling Kindersley.
Wade,L.G.2006.Organic Chemistry Sixth Edition.USA:Pearson Prentice Hall.