EXPERIMENT REPORT

ORGANIC CHEMISRTY II
ALDEHYDE AND KETONE

BY :

META WIDYAS KARTIKA

(083194003)

DEWI RACHMAWATI

(083194012)

SEFFI DIAN S

(083194024)

ASROFIYAH

(083194037)

PENDIDIKAN KIMIA PLUS 2008

JURUSAN KIMIA
FAKULTAS MATEMATIKA DAN ILMU PENGETAHUAN ALAM
UNIVERSITAS NEGERI SURABAYA
2010

A.

TITLE

: Aldehydes And Ketones Reactions

B.

OBJECTIVES :
1. Know the principle reaction of carbonyl compounds
2. Know the difference reaction to aldehydes and ketones
3.
Know the type of simple chemical test to distinguish aldehydes and ketones

C.

BASIC THEORY
The carbonyl group consists of a carbon atom bonded to an oxygen atom by a double

bond.Compounds containing a carbonyl group are called carbonyl compounds. This group
includes the aldehydes and ketones (deninston, 2003: 393). Aldehydes and ketones are one of
the oxidation products of the alcohols. Each of these compounds contain a carbonyl group (a
carbon atom double bonded to an oxygen atom).
In aldehydes the carbonyl group is always located at the end of the carbon chain
(carbon-1). In ketones the carbonyl group is located within the carbon chain of the molecule.
Thus, in ketones the carbonyl carbon is attached to two other carbon atoms. However, in
aldehydes the carbonyl carbon is attached to at least one hydrogen atom; the second atom
attached to the carbonyl carbon of an aldehyde may be another hydrogen or a carbon atom.

The structure of aldehydes and ketones. (a) The

general structure of an aldehydes and a ball-andstick model of the aldehyde propanal. (b) The
general structure of a ketone and a ball-and stick
model of the ketone propanone.
Aldehydes and ketones are polar compounds because of the polar carbonyl group.
Because of the dipole-dipole attractions between molecules, they boil at higher temperatures
than hydrocarbons or ethers that have the same number of carbon atoms or are of equivalent
molecular weight. Because they cannot form intermolecular hydrogen bonds, their boiling
points are lower than those of alcohols of comparable molecular weight.

The presence of hydrogen atoms, it makes aldehyde is easily oxidized or in other

words, the aldehyde is a strong reducing agent. Because ketones do not have this particular
hydrogen atom, it is very difficult to oxidize ketones. Only a very strong oxidizing agent such
as a solution of potassium manganate (VII) (potassium permanganate solution) that can
oxidize ketones - and even then with a mechanism that is not neat, with a break C-C bonds .
Usually aldehydes react faster than ketones toward a similar reagent. This is because
the atoms of the aldehyde carbonyl is more strongly protected than the atoms of the carbonyl
of ketones.to difference aldehyde and ketone was use :
Tollens reagent (silver mirror test)
Tollens reagent containing, [Ag (NH3) 2]OH. Tthis compound is made from a solution
of silver (I) nitrate. This compound formed by inserting a drop of solution of sodium
hydroxide to a solution of silver (I) nitrate produces a precipitate of silver (I) oxide, and then
add just enough dilute ammonia solution to dissolve the re-deposition.
To perform the test with Tollens reagent, a few drops of aldehyde or ketone is inserted
into the newly created Tollens reagent, and heated slowly in a hot water bath for several
minutes. Aldehyde give a colorless solution produces a precipitate of silver gray, or a silver
mirror in the test tube and ketone is no change
Aldehyde reduct silver ion in [Ag (NH3) 2]OH to silver metal. Because the solution is
alkaline, it is itself oxidized to aldehyde with a salt and form carboxylic acid.
Half-reaction equation for the reduction of ion diamminperak (I) to silver are as
follows:
And the equation half-reaction of oxidation of an aldehyde in alkaline conditions, ie
With combining teo of them will produce a complete reaction equation:
The use of Fehling solution or Benedict's solution
Fehling solution and Benedict's solution is a variant of which is ensensial same
solution. Both contain copper ions (II). Fehling solution containing copper ions (II)
dicompleks with tartrate ions in the solution of sodium hydroxide. Complexing ion copper (II)
with tartrate ions to prevent the deposition of copper (II) hydroxide.
Benedict's solution containing copper ions (II) which form complexes with citrate ions
in a solution of sodium carbonate. Again, Complexing the copper ions (II) can prevent the
formation of a precipitate - this time deposits of copper (II) carbonate. Fehling solution and
Benedict's solution used in the same way. A few drops of aldehyde or ketone is added to the
reagent, and the mixture is heated slowly in a hot water bath for several minutes. Reaction
with aldehide form solution produced a dark red precipitate of copper (I) oxide, and ketone

was no change. This reaction because aldehyde reduction of copper ions (II) to copper (I)
oxide. Because the solution is alkaline, it is itself oxidized to aldehyde with a salt of the
corresponding carboxylic acid. The equation of the reaction is:
And the equation for the oxidation of aldehydes in the alkaline condition

Combining two of them will get :

Testing with fenilhidrazin

Testing with this compound describes the reaction of aldehydes and ketones with 2,4dinitrophenylhydrazine, benzadehida and sikfoheksanon as a test reaction to double bond C =
O. Here we also discuss briefly about some other similar reaction known as additionelimination reaction (or condensation).
2,4-dinitrophenylhydrazine often abbreviated to 2,4-DNP or 2,4-DNPH. 2,4dinitrophenylhydrazine solution in a mixture of methanol and sulfuric acid reagent known as
Brady. In fenilhidrazin, one hydrogen atom in the hydrazine was replaced by a phenyl group,
C6H5. It is based on a benzene ring.

Reaction
With enter a few drops of aldehyde or ketone, or it could be a solution of aldehyde or
ketone in methanol, into the reagent fenil hidrazin. The formation of yellow or bright orange
precipitate indicated a C = O double bond in an aldehyde or ketone.
The reaction of this test is the simplest to an aldehyde or ketone.
H

+ H2O(l)

(s)

1-benzylidene-2-phenylhydrazine

H
C

O
C

H
C

(aq)

H
H

N
H

N
N
1-benzylidene-2-phenylhydrazine
C
N
N
C
N

H
H

H
H

Benzaldehyde

H2N

(aq)
+ CH3OH(aq)
1-benzylidene-2-phenylhydrazine
1-benzylidene-2-phenylhidrazine
(aq)

(Yellow Crystal)
Phenylhydrazine

(aq)

(s)
(s)

This reaction is known as the condensation reaction. Condensation reaction is a

reaction in which two molecules join together accompanied by the loss of a small molecule in
the process. In this case, the small molecule is water. Addition-elimination reaction of
aldehydes and ketones have two uses in testing aldehydes and ketones.
This reaction can be used to test the existence of double bond C = O. C = O double
bond in an aldehyde or ketone have only orange or yellow sediment.
1. This reaction can be used to help identify a particular aldehyde or ketone.
2. The precipitate was filtered and washed with, for example, methanol and then
recrystallized from a suitable solvent, which solvent can calm vary depending on the
nature of aldehydes and ketones. For example, we can merekristalisasi products small
aldehydes and ketones from a mixture of ethanol and water.
The crystals that formed were dissolved in hot solvent with a minimum amount. If the
solution has cooled, the crystals precipitated again and can be filtered, washed with a little
solvent and dried. These crystals will be pure. If you know the melting point crystals, then
you can compare it with the theory.
Haloform Reaction
Bromine and chlorine also reacts with methyl ketone produces bromoform and
chloroform (its formation is not useful to test the reaction because of bromoform and
chloroform is a liquid that is not obvious). A general term to refer CHX3 is haloform
(haloform reaction) (Fessenden, 1982). Iodoform test is a typical test for methyl ketone
compounds. Hydrogen in alpha position is acidic and its use produces results enolate
anion. Further enolate anion can react with the halogen compound halokarbonil for iodine.
O

H3C

O
CH3

+ 3I2 + 3OH-

propan-2-one

H3C

C
OH

acetic acid

CHI3

+ 3I- + H2O

Iodoform
(yellow precipitate)

Aldol condensation
Aldol condensation is a fusion reaction in the atom or molecule in which different molecules
and form new compounds are more complex. In general, condensation reactions occur in the
liberation of water, alcohol, or other compounds that stabiol. Komndensasi aldol reaction
occurs in the aldehyde-aldehyde having an alpha H atoms, namely H atoms are bound by the
C atoms directly bonded to the carbonyl group, when reacted with dilute alkali (NaOH) or
ZnCl2. In compound 3-hydroxy butane there are two functional groups, namely group-CHO
and-OH groups. Therefore, these compounds have properties such as aldehydes and alcohols.

From the word aldehyde and alcohol of said aldol. 3-hidrosibutanal When heated, the
dehydration process occurs and produces krotonaldehida. The example with acetaldehyde is :

O
H3C

H3C

H3C

CH

CH2

H3C

heat
H2O

D. EQUIPMENT AND SUBSTANCES

2.

Equipment
Test tube
Thermometer
Conical flask 50 ml
Hirsch funnel
Buchner funnel
Filter paper
Rubbing alcohol burner
Spherical flask
Refluks
Substances
Acetaldehyde
Cyclohexanon
Formalin
Isopropyl alcohol
Methanol
Ethanol
Fehling reagent
NaOH 10 % sulotion
NaOH 5% sulotion
AgNO3 5% sulotion
NH4OH 5% sulotion
NaHSO3 saturated
HCl sulotion
Phenylhidrazyn reagent
Iodium solution
Cool water

CH2

adol

1.

CH

H+
H-

OH

O-

CH3

O
CH

CH

crotonaldehyde

 Pipe kapiler

E. PROCEDURE
1. Tollens test
a. make tollent reagent
2 ml AgNO3 5%
3
-

Pour to test tube

Pour 2 drops NaOH 5%
Mixed well the mixture

Form brown
precipitate
-

Add NH4OH 2% drop by drop and still shake until the precipitate can soluble
precisely

Precipitate soluble
Tollens reagent
b. Test with tollens reagent
Prepare 4 test tube

Prepare 4 test tube

Test tube
Test tube
Test tube
Test tube
A
B
C
D
- Add 2 drops
- Add 2 drops
- Add 2 drops
- Add 2 drops
Benzaldehide
Acetone
Cyclohexanone
Formalin
Test tube
A

Test tube A
There is a
2. Fehling
test
grey clump
which
Testdrift
tube A
There is a dark red
precipitate and by the
time change into
cuprum mirror

- Shake the mixture carefully

Test tube
Test tube
Test tube
- Rest for 10 minutes
heat the test tube
B - If there isnt reaction,
C
D in water bath
(35C - 50C) for 5 minutes

Test tube B
There isnt
reaction
Test tube B
(not
available)

Test tube C
There isnt
reaction
Test tube C
There isnt
reaction

Test tube D
There is
silver mirror
in around
Testtest
tube D
tube wall
There isnt
reaction

- Add 5 ml Fehling solution in each test tube

- Add 2 drops
Formaldehyde

- n- Heptaldehyde
(not available)

- Add 2 drops
Acetone

- Add 2 drops
Cyclohexanone

- Put into boiling water for 10-15 minutes

3. Bisulfit adition

5 ml phenyl hydrazyn

5 ml saturated solution
- NaHSO
Test tube
Test tube
of
3
- Pour in conical
flask 50 ml
A
B
- Cooled in ice water
- Add 2,5 ml acetone drop by drop with shaken for 5 minutes
- After 5 minutes, add 10 ml ethanol for start crystalisation

White -crystal
Filter that crystal with separating funnel
- Add strong HCl with drop by drop carefully
Test tube
A
Observation
result:
The crystal was lost
and the solution is
4. Test with colorless
Phenilhydrazin
Form yellow
crystal

Test tube
B

There isnt
reaction
- Add into each test tube

The melting
point is 134C

- Add 10 drops Benzaldehyde

- Add 10 drops Cyclohexanone

- Close the test tube

- Shake strongly for 1-2 minutes until made crystal

Filter the crystal with filter paper in funnel

Wash the crystal with cold water clean the crystal
Add methanol drop by drop for make crystal again
Rested the crystal until dry (about 2 days)
Determine the melting point

gram hydroxylamine
5. Oxim 1making
(the substances is not available)
hydrocloryne

Add 1,5 gram crystal CH3COOH

Pour 4 ml water
Dissolve in conical flask 50 ml
Heated until 35C
Add cyclohexanone drop by drop
Close the flask
Shake for 2 minutes until cyclohexanone oxim can form

Observation result

- Cooled the flask in ice water, then filter the crystal with funnel
- Wash with ice water and put on dry filter paper
- Determine the melting point

6. Haloform reaction

3 ml solution of NaOH 5%
- Add in each test tubes

Test tube
Test tube
Test tube
Test tube
A
B
C
D
- Add 5 drops Acetone - Add 5 drops isopropyl - Add 2-pentanone - 3-pentanone
Alcohol
Not Available
- Add iodium and shaken until the color of iodium not change again

Test tube A
There are yellow
precipitate (++) and the
smellcondensation
like medicine
7. Alcohol

Test tube B
There are yellow
precipitate (+++) and the
smell like medicine

a. Make krotonaldehyde

4 ml NaOH 1%
- Put into test tube
- Add 0,5 ml acetaldehyde
- Shaken well and note the smell (from acetaldehyde before reaction)
The smell like
- baloon
Boiled the mixture for 3 minutes and carefully
- Note the smell

Krotonaldehyde
The smell is rancid

b. Determine the melting point (Not Available)

10 ml Ethanol
- Put into conical flask 50 ml
- Add 1 ml acetone
- Add 2 ml benzaldehyde
- Add 5 ml NaOH 5%
- Refluks the mixture for 5 minutes
- Cool the flask and collect the crystal produce by Buchner funnel
- The mixture can make crystal again from ethanol
- Determine the melting point

Melting point

F. OBSERVATION RESULT
No
1.

Treatment
Test with Tollens Reagent
In the test tube, add 2 ml

Before
AgNO3 5%

Observation Result
After
= AgNO3 + NaOH form

Colorless

precipitate. The colour is

AgNO3 5% and 2 drops NaOH NaOH 5%

5%. After that, mixed well the
Colorless

dark brown.
After the mixture add

mixture. Add NH4OH 2% drop NH OH 2%

4
by drop and still shake until the
Colorless

NH4OH 2%,the precipitate

precipitate

can

soluble

precisely. The mixture is call

tollens reagent.
Prepare 4 test tube
Benzaldehyde =
A : Benzaldehyde (2 drops) + 1
yellow pure
ml Tollens

soluble.
Add NH4OH 41 drops.
The color of that mixture
is colorless.
After the mixture, test tube
:
A : form white precipitate
and become grey
B : There isnt precipitate

B : Acetone (2 drops) + 1 ml Acetone

Tollens
C : Siclohexanon (2 drops) + 1
ml Tollens
D : Formalin (2 drops) + 1 ml
Tollens
2.

Test with Fehling Reagent

Make Fehling solution (Fehling
test), 10 ml Fehling A + 10 ml
Fehling B.
Prepare 4 test tube, 2 drops
solution test and 5 ml Fehling
A : Formaldehid + Fehling + heat
10 minutes
B : Aseton + Fehling + heat 10

colorless
Siclohexanon
Formalin

and

the

solution

is

colorless,by the time the

=

colorless

color change to blue.

C : The solution is colorless
D : form silver mirror

colorless
Fehling A : Light Mixture of Fehling A + B:

Solution is dark blue

Blue

Contain Cu2+
Fehling
B
:
A : The solution is blue
Colorless
and there are precipitate.
Formaldehyd
:
The color is dark-red and
Colorless
by the time,form cuprum
Acetone
:
mirror.
Colorless
B : There is no reaction,

minutes
Siclohexanon
C : Siclohexanon + Fehling +
Colorless
heat 10 minutes
D : n-Heptanal (The solution is
not available)
3.

the solution is still dark

blue.
C : There is no reaction,
the solution is still dark
blue.

Bisulfit Adition
= After cooled in water, the
solution still colorless.
Colorless
sodium bisulfite, NaHSO3.
After add acetone, the
Cool in water
Water = Colorless
solution is colorless.
Add 2,5 ml acetone drop by
Acetone
= After add etanol 96%, the
drop and shake well for 5
Colorless
solution make a crystal,the
minutes.
HCl = Coloress
color is white.
Add 20 ml ethanol 96% for
Etanol 96% = After add HCl, the crystal
make crystal
Colorless
is lost and there are only
Filter the crystal
Add strong HCl drop by drop in
solution which colorless.

Add 5 ml saturated solution of NaHSO3

4.

the crystal.
Test with Phenylhidrazin
A : there are solution ,the
5 ml phenylhidrazin add in 2 Phenylhidrazin =
color is orange and there
Orange
test tube
A : 2,5 ml Phenylhydrazin + Benzaldehyde =
are turbit yellow crystal.
B : There is not reaction,
Benzaldehyde
Yellow pure
B: 2,5 ml Phenylhidrazin +
so only there are orange
Siclohexanon =
Siclohexanon
solution.

 After that close the test tube and

Crystal in test tube A

Colorless

Metanol
shake strogly.
Filter the crystal with separating
Colorless
funnel.
Cold Water
Wash with cold water,next
Colorless
Wash with methanol
Rasted and determine the melt

separated with funnel.

Crystal in test tube A =

Yellow Turbid (++).

After add cold water, the
crystal are little soluble
and the color is yellow (+

point

+)
After add methanol, the
crystal

which

little

soluble,form crystal again

and the color is yellow but
more white.
The melting

point

is

132OC.
5.

Haloform Reaction
3 ml solution of NaOH 5% put NaOH
into 2 test tube.
A : Aceton + Iodium
B : Isoprophyl Alcohol
Iodium

5%

Colorless
+

= A : When NaOH +
Aceton,the solution is

Iodium = Dark
Brown
Yellowish
Aceton
Colorless

Colorless.
B : When
Isopropyl

NaOH

Alcohol,

+
the

solution is Colorless.
= After add iodium
A : The solution change

Isopropyl Alcohol

into turbid solution and by

= Colorless

the time ,the color of

solution change into dark
brown

yellowish

like

iodium.
There are precipitate,the
color is yellow. (need 2 ml
Iodium)
B : Like test tube A,after
add iodium the solution is
turbid,

by

the

time

solution change into dark

brown
Iodium.

yellowish
(need

like
2

ml

Iodium)
There are precipitate and
the color is yellow.
The different of test tube A
and B, there are :
A : Little Precipitate
B : Much Precipitate
6.

Alcohol condentation
4 ml NaOH 1% put into test NaOH
tube
Add 0,5 ml acetaldehyde
Shake well
Boiled the mixture for
minutes

1%

Colorless
Acetaldehyde
3

= The mixture form solution

and the color is yellow (+
=

Colorless,
the smell like
baloon

+).
The smell is pungent.

PICTURES ABOUT ALCOHOL AND KETONES EXPERIMENT :

1. Tollent reagent

Picture 1: reaction between formalin and tollent reagen

With the tollent reagent, formaline (formaldehyde) can make silver
mirror precipitate.

2. Fehling reagent

Picture no.2 :

formaldehyde, acetone, and siclohexanone when

react with fehling reagen

Picture no.3 : acetone and siclohexanone not

react with fehling

Ketone cant be react with fehling agent

Picture no.4 : Formaldehyde react with fehling

Aldehyde compounds can react with fehling to form dark red
precipitate.

Picture no.5 : Formaldehyde which experiences more oxidation

When aldehyde compounds more oxidation, so they can form cuprum mirror in the
wall of tube.

Picture no. 6: reaction benedict with formaldehyde

Benedict is slower than fehling. So if they react with fehling, so they are not react
fastly.
Although, if aldehyde compounds react with benedict, they must be to form dark red
precipitate too.

3. Bisulfite adition

Picture no. 7 : reaction between NaHSO3 + Acetone with

ethanol
In
it

this reaction, after NaHSO3 + Acetone add some ethanol,

is form crystal which the color is white.

Picture no. 8 : result when compound pict.7 add strong

HCl
When solution picture 7 add some strong HCl, so that the
solution will be colorless.

4. Test will phenylhydrazyn

Picture no.9 : solution of phenylhydrazyn

Picture no.10 : reaction between phenylhydrazyn with

benzaldehide
When phenylhydrazyn react with benzaldehyde, it make precipitate
which color is yellow.

Picture no.11 : reaction between phenylhydrazyn with siclohexanone

Siclohexanone cant be reart with phenylhydrazyn.

Picture no.12 : result of the phenylhidrazon

5. Haloform reaction

Picture no.13 : compare acetone and isopropyl alcohol when

add iodium in NaOH

The result of this paper is that in acetone is contain more

precipitate than isopropyl alcohol and the color is more dark than
isopropyl alcohol

6. Alcohol condensation

Picture no.14 : the result of reaction between

Acetaldehyde with NaOH

G. ANALYSIS
1. Tollens Reagent Test
1.1 Prepare tollens Reagent.
First, add 2 ml AgNO3 5% and 2 drops NaOH 5% in the test tube. This produce is
brown precipitate Silver Oxide (Ag2O). Then, it is added drop by drop NH 4OH
2% until sediment soluble precisely, is signed with disappeared brown sediment
and solution becomes colorless. The compound formed here is 2Ag[(NH3)2]OH .
If the solution is add ammonium hydroxide too much, testing to differences
aldehyde and ketone with this reagent will be fail.
Reaction :
2AgNO3 + 2NaOH
Ag2O + 2NaNO3 + H2O
Ag2O

+ 4NH4OH

2Ag[(NH3)2]OH + 3H2O
Brown

1.2 Distinguish Aldehydes and Ketones with tollens reagent

The next procedure is prepare 4 test tube (test tube A, B, C, and D) and fill with
Tollent Reagents, then filled each test tube with 2 drops of benzaldehyde in test tube
A, 2 drops of acetone in test tube B, 2 drops of cyclohexanon in test tube C, and 2
drops of formalin in test tube D. Shake and rest it for ten minute, if there are no
reaction, place in water bath for 5 minutes to speed up reaction. And the result of this
experiment are:
Test Tube A : Form white lump drift in solution and become orange when heated. It
show that Silver (Ag) was formed, because Tollens Reagent (Ag[NH 3]2)OH) can
oxidize benzaldehyde become Benzoic Acid and become silver (Ag) in test tube
A. Silver Mirror in test tube A was disappeared because the properties of
benzaldehyde is contain oils.
Reaction In Test Tube A:
O

+ Ag(NH3)2OH Ag

OH

benzoic acid

benzaldehyde

+ NH3 + NH4+ + H2O

Test Tube B : Solution is colorless and not form silver mirror because acetone can not
oxidation by Tollent reagent.
Reaction :
O
C
H3CAcetone

CH3 + AgNH32OH no Reaction

Test Tube C : Solution is colorless and not form silver mirror because siclohexanon
can not oxidation by Tollent reagent, but a long time, it change become blue
color.
Reaction:
O

+ AgNH32OH no Reaction

Siclohexanon
Test Tube D : Form Silver Mirror in wall of Test Tube. It is Silver (Ag), because
Formalin can reduction Tollens Reagent (Ag[NH3]2)OH) becomes Silver and
Formalin oxidation becomes Formiat Acid.
Reaction:
O

C
H between
H
The C
aim of
+ this
AgNH
experiment
differenteate
aldehyde
+ H2O + and
NH4+keton
+ NHby
32OH Ag
3 testing
H
OH
Tollens Reagent.

2. Test with Fehling Reagent

The first, prepare Fehling Reagent by mixturing Fehling A (CuSO 4) and Fehling B
(NaOH + Sodium Potassium Tartarat). Fill Reagent in 3 test tubes (Test tube A,B, and
C), then add each test tube with formaldehyde, acetone and siclohexanon. Place the
test tube in water bath and heat for 10-15 minutes. The heating is used to speed up
reaction. The result of this experiment:
Test tube A: The color of solution is blue, form dark-red sediment and by the time
also form cuprum mirror. Formaldehid can oxidation becomes Formiat Acid and
Cuprum(II) Oxide can reduction becomes Cuprum(I) Oxide. If cuprum excessive
oxidation because heating , it will form cuprum mirror.
Reaction:
O

+ CuO

+ Cu2O

+ H2 O

H Solution has blue color and not

Test tube B:
OHform dark-red sediment because acetone
dark-red sediment
can not oxidation by Fehling reagent.
Reaction:
O

Test tube C: Solution has blue color and not form dark-red sediment because
C
CH
H3C siclohexanon
+ CuO
no
can3 not
oxidation
byreaction
Fehling reagent.

Reaction:

+ CuO no reaction
The aim of this experiment differentiate between aldehyde and keton by testing
Fehling Reagent.
Note:
We also use benedict reagent, but when react with solution A (Benzaldehyde) not
form dark-red precipitate. It occurs because the benedict reagent is not too reactive.
So, the reaction is slower than Fehling Reagent. It need a long time for happen
reaction.
3. Bisulfit Addition
Connical Flask 50 ml filled 5 ml the bored sodium bisulfit solution and cool in ice
water. The process of cooling must be done carefully to avoid freezing. Then, add 2,5
ml acetone drop by drop with shake. After five minutes,add 10 ml etanol for starting
crystalitation. The color of crystal is white . The crystal is sodium 2-hydroxipropane2-sulfonate. Then, add many drops of strong clorida acid to form acetone again. The
reaction is reversible.
Reaction:
O

H3C

OH
CH3 + NaHSO3 + C2H5OH H3C

CH3

SO3Na

Acetone

Sodium 2-hydroxypropane-2-sulfonate
O

OH

H3C

CH3

+ HCl

H3 C

CH3

propan-2-one
SO3Na

sodium 2-hydroxypropane-2-sulfonate
The aim of this experiment is showing the differences of aldehyde and keton.
Especially, the bisulfite nucleofilik addition reaction of acetone.
4. Test with phenylhidrazin
First, two test tube filled 5 ml phenylhydrazine and each filled with 2,5 ml test
solution (Benzaldehyde and Siclohexanon) and shake for 1-2 minutes in order to
solution can mixture perfectly and form crystal. Then, filter the solution to separate

crystal and filtrat. The crystal is 1-benzylidene-2-phenylhydrazine. Wash the crystal

with water. It make the crystal little soluble. To make crystal again, add little
methanol. Methanol and water act as solvent. Next, determine melting point of the
crystal with block logam. To determine it, we must wait three days in order to the
crystal really dry and pure. This reaction is called Condensation reaction, the fusing of
two moleculs form an molecul with free water molecul (H 2O). The Result of this
experiment :
Test Tube A : Solution has orange color and form yellow crystal. The yellow sediment
is 1-benzylidene-2-phenylhydrazine. There are yellow crystal to show a carbonil
compounds. The initial melting point is 120OC and it is constant at 132OC.

O
C

H2N

Reaction:

(aq)

(aq)

Benzaldehyde

Phenylhydrazine

N
H

(s)

1-benzylidene-2-phenylhydrazine
H
C

(Yellow Crystal)
N

N
H

+ H2O(l)
(s)
H

1-benzylidene-2-phenylhydrazine
C

(Yellow Crystal)

N
H

(aq)

H
C

1-benzylidene-2-phenylhydrazine
N
H

+ CH3OH(aq)
(aq)

methanol

1-benzylidene-2-phenylhidrazine

N
H

(s)

1-benzylidene-2-phenylhidrazine
(Pale Yellow Crystal)

Test tube B : Solution has orange color and not form yellow sediment. The solution is
Phenylhydrazine.
Reaction:
H
O +

H2 N

no reaction
(aq)

(aq)
Siclohexanon

The aim of this experiment is testing a carbonil compounds and differences

between aldehyde and ceton.
5.

Haloform Reaction.
There are 2 test tube.
Test tube A contain 3 mL sodium hydroxide 5 % colorless and add 5 drops acetone
colorless. In this reaction the solution is colorless. After that add iodium solution (dark
brown yellowish) until the color of iodium not ceace (need 2 mL iodium). The
solution change into turbid solution and by the time the color of solution change into
dark brown yellowish like iodium and form yellow precipitate in base of tube. This is
iodoform. When iodoform is formed, there are sting smell. This smeel is special smeel
of iodoform. This reaction equation is:

H3C

O
CH3

propan-2-one

+ 3I2 + 3OH-

H3C

C
OH

acetic acid

CHI3

+ 3I- + H2O

Iodoform
(yellow precipitate)

Test tube B contain 3 mL sodium hydroxide 5 % colorless and add 5 drops isoprophyl
alcohole colorless. In this reaction the solution is colorless. After that add iodium
solution (dark brown yellowish) until the color of iodium not ceace (need 2 mL
iodium). Like test tube A, after add iodium is turbid, by the time the solution change
into dark brown like iodium and form yellow precipitate in base of tube. This is
iodoform. When iodoform is formed, there are sting smell. This smeel is special smeel
of iodoform. This reaction equation is:

H3C

CH3

CH

I2
OH-

H3C

C
acetone

OH
isoprophyl alcohole

O
H3C

CH3

I2
OH-

CH3

H3C

acetone

acetic acid

+
OH

2 CHI3
iodoform
yellow precipitate

6. Aldol Condensation
4 mL sodium hydroxide 1 % colorless put in test tube and add 0,5 mL acetaldehyde
colorless. After that shake well. The smell in this rection is like baloon (this smell is
smell of acetaldehyde that not be react). This reaction equation is :
O
H3C

OH-

H3C

acetaldehyde

acetaldehyde

After that boiling the mixture during 3 minutes and carefully. The color of mixture is
be yellow and this smell is pungent. It show that this mixture experince condentation
and formcrotonaldehyde. This reaction aquation is :
O
H3C

O
H

H3C

H3C

CH

CH2
adol

CH

CH2

H
H+
H-

OH

H3 C

O-

heat
H2O

CH3

O
CH

CH

crotonaldehyde

H.

DISCUSSION
In the first experiment (tollens test), there are deviation between the result of

experiment with theory. Base on theory aldehyde (benzaldehyde) is positive reaction with
tollens reagent and form silver mirror. But in our experiment it not happen. In our experiment,
reaction between bezaldehyde with tollens reagent form white hank and became grey hank. It
is caused by the properties of benzaldehyde is similar with oil, so cohession process with the
wall-tube do not happen.
In the second experiment (fehling test), when we use benedict reagent to oxidazing
aldehyde to form dark red sediment, tis reaction is longer than use fehling test. It may be this
benedict reagent is made more long, but fehling reagent is new made.
In the fourth experiment (testing with phenylhydrazin), based on theory the melting
point of benzaldehyde phenylhydrazon is 156 oC. But from our result we get the melting point
of benzaldehyde phenylhydrazon is 132 oC. It is caused not so pure the crystal of substances
and because it heaped up with other crystal that wet, so it is not so dry.

I.

CONCLUSION
After we did experiment, we get conclusion:
1. Benzaldehyde and formalin (aldehyde) is oxidazed with reagent tollens and form
silver mirror, but acetone and siclohexanone (ketone) is not.
2. Formaldehyde (aldehyde) is reacted with reagent fehling and form dark red
precipitate and if cuprum is more oxidazing (with heating), it will form cuprum
mirror. But aceton and siclohexanone (ketone) is not be oxidation.
3. Ketone (acetone) react with Sodium bisulphite form Keton (asetone) bisulphite as
salt (that is not dissolved in organic solvent). It form white hablur.

4. Benzaldehyde (aldehyde) is react white phenylhydrazin and form hablur. After this
hablur is react with etanol is form yellow sediment. But siclohexanone with
phenylhydrazin and etanol not form yellow sediment.
5. Acetone (ketone) is react with iodium and form iodoform. Iodoform is yellow
precipitate and has specific smell.
6. Asetaldehyde (aldehyde) experience condentation and form crotonaldehyde. The
color of Crotonaldehyde is yellow and has pungent smell.

J. ANSWER OF QUESTION
1. a. Reaction of Tollens with Formaldehid
O

+ AgNH32OH Ag H
H

+ H2O + NH4+ + NH3

OH

b. Reaction of Fehling with Heptaldehyde

H3C

H2
C

H2
C

H2
C

H2
C

H2
C

+ CuO C6H13

c. producing of addition compounds of aceton-bisulfite

O

H3C

OH
CH3 + NaHSO3

H3C

CH3

SO3Na

d. producing of benzaldehyde phenylhydrazon

H

O
C

H2N

(aq)

(aq)
H
C

N
H

+ Cu2O + H2O

e. producing of siclohexanon oxim

OH
O

NOH

+ H2NOH

NHOH

f. testing iodoform at 2-pentanon

O
CH3

H2
C

CH2

CH3 + 3I2 + 3OH-

CH

O
CH3

CH2

C
H2

2.
H3C

H3 C

H3C

CH

CH2

H3 C

CH

CH2

H
H+
H-

OH

O-

O
H

CI3 + 3H2O + 3I-

heat
H2 O

CH3

O
CH

CH

crotonaldehyde

adol

3. Yes, it can

identify CH3 - CH2 - OH, used triiodometana (iodoform)

heat

R - OH + I2+ OH-

CHI3 (yellow sediment)

Just, secunder alchohol can produce CHI3 (triiodometana) but etanol is the only
kind of simple prymer alcohol that can be known.

It can differences between isopropyl alcohol and n-butil alcohol for isopropyl
alcohol. It can produce CHI3 because it is secunder alcohol. But, n-butil
alcohol can not produce CHI3 because it is prymer alcohol.

4. To differences between aldehid and ketones.

5.

a. by using iodoform testing, we can differences 3-pentanon and 2-pentanon can

produce yellow sediment (CHI3) but 3-pentanon can not produce yellow sediment
(CHI3).
b. testing iodoform, 3-pentanon can produce yellow sediment (CHI 3) but pentanol
cannot produce yellow sediment (CHI3).
c. reaction of benzaldehyde with tollen regent or fehling reagent is positive.. it can
oxidation. But acetofenon with tollen regent or fehling reagent is negative. It
cannot oxidation.

6.

Keton react with Sodium bisulphite

form Keton bisulphite

as salt that is not

dissolved in organic solvent

This Reaction is
O

OH

CH3 C CH3 + NaHSO3

CH3 C CH3

Na3SO

Acetone

sodium bisufit

acetone bisulfit

If the Acetone bisulphit is reacted with chloride acid, it will be Acetone, Sodium
chloride, and water.
This Reaction is
OH

CH3 C CH3

+ HCl

CH3 C CH3 + NaCl

+ SO2 + H2O

Na3SO
acetone bisulfit Chloride acid Acetone

sodium chloride

7. Based on theory:

the melting point of penilhydrazon is 19,5o

the melting point of 2,4-dinitrophenylhydrazon is 198-202oC

So, the meltig point of 2,4-dinitrophenylhydrazon is higher than phenylhydrazon.

the melting point of benzaldehyde penilhydrazon is 156oC

the melting point of benzaldehyde 2,4-dinitrophenylhydrazon is 239-241oC

So, the meltig point of benzaldehyde 2,4-dinitrophenylhydrazon is higher than

phenylhydrazon.
8. The rule of sodium acetat is to pull hydrogen

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Ir. Darjanto,dkk. 1988. Himpunan Bahan Kuliah Ilmu Kimia Organik. Purwokerto :
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Wilbraham dan Matta. 1992. Pengantar Kimia Organik dan Hayati. Bandung : ITB.
H, Hard. 1989. Kimia Organik Untuk Universitas. Jakarta : Erlangga.
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Aldehid

dan

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http://www.chem-is-

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