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A.

Experiment tittle : Aldehyde Ketone and Carboxylic Identification


B. Experiment date : March, 5th 2018 on 10.20 am-04.20 pm
C. Experiment purpose : 1. To identify the aldehyde group in organic compounds.
2. To identify the ketone group in organic compounds.
3. To identify the carboxylic group in organic compounds.
4. To differentiate the aldehyde group, ketone group, and
carboxylic group in organic compounds
D. Basic theories :

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. Formaldehyde is
the simplest aldehyde, with two hydrogen atoms bonded to the carbonyl group.
Ketones and aldehydes are similar in structure, and they have similar properties.
There are some differences, however, particularly in their reactions with oxidizing agents
and with nucleophiles. In most cases, aldehydes are more reactive than ketones, for
reasons we discuss shortly.
The carbonyl carbon atom is hybridized sp2 and bonded to three other atoms
through coplanar sigma bonds oriented about 120° apart. The unhybridized p orbital
overlaps with a p orbital of oxygen to form a pi bond. The double bond between carbon
and oxygen is similar to an alkene C=C double bond, except that the carbonyl double
bond is shorter, stronger, and polarized.
IUPAC Names Systematic names of ketones are derived by replacing the final -e
in the alkane name with -one. The “alkane” name becomes “alkanone.” In open-chain
ketones, we number the longest chain that includes the carbonyl carbon from the end
closest to the carbonyl group, and we indicate the position of the carbonyl group by a
number. In cyclic ketones, the carbonyl carbon atom is assigned the number 1.
Systematic names for aldehydes are derived by replacing the final -e of the alkane
name with -al. An aldehyde carbon is at the end of a chain, so it is number 1. If the
aldehyde group is a substituent of a large unit (usually a ring), the suffix carbaldehyde is
used.

A ketone or aldehyde group can also be named as a substituent on a molecule


with a higher priority functional group as its root. A ketone or aldehyde carbonyl is
named by the prefix oxo- if it is included as part of the longest chain in the root name.
When an aldehyde -CHO group is a substituent and not part of the longest chain, it is
named by the prefix formyl. Carboxylic acids frequently contain ketone or aldehyde
groups named as substituents.

Common Names As with other classes of compounds, ketones and aldehydes


are often called by common names instead of their systematic IUPAC names. Ketone
common names are formed by naming the two alkyl groups bonded to the carbonyl
group. Substituent locations are given using Greek letters, beginning with the carbon next
to the carbonyl group.
Some ketones have historical common names. Dimethyl ketone is always called
acetone, and alkyl phenyl ketones are usually named as the acyl group followed by the
suffix -phenone.

Common names of aldehydes are derived from the common names of the
corresponding carboxylic acids (Table 18-2). These names often reflect the Latin or
Greek term for the original source of the acid or the aldehyde. Greek letters are used with
common names of aldehydes to give the locations of substituents.
(Wade, J.R. 2013)

In general, aldehydes and ketones have higher boiling points than alkenes because
the dipole–dipole attractive forces between molecules are stronger. But they have lower
boiling points than alcohols because, unlike alcohols, two carbonyl groups can’t form
hydrogen bonds to each other.

The carbonyl oxygen of aldehydes and ketones can form hydrogen bonds with the
protons of OH groups. This makes them more soluble in water than alkenes, but less
soluble than alcohols.
To the synthetic chemist, the most important of these are the last two: the
oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. Indeed,
when combined with reactions that yield alcohols, the oxidation methods are so versatile
that it will not be necessary to introduce any new methods for preparing aldehydes and
ketones in this chapter. A few examples will illustrate this point. Let’s first consider how
to prepare an aldehyde from a carboxylic acid. There are no good methods for going from
RCO2H to RCHO directly. Instead, we do it indirectly by first reducing the carboxylic
acid to the corresponding primary alcohol, then oxidizing the primary alcohol to the
aldehyde.

(Francis, A Carey. 2008)

E. Tools and materials :


1. Tools:
a. test tube 17 pieces
b. thermometer 1 piece
c. Erlenmeyer 1 piece
d. Hissan Funnel 1 piece
e. Buncher funnel 1 piece
f. Bunsen burner 1 piece
g. round shape flask 50 mL 1 piece
h. reflux condenser 1 piece
i. filter flask + filter paper 1 piece
j. Caliper pipe + metal block 1 piece
2. Materials:
a. benzaldehyde 12 drops
b. acetone enough
c. n-heptaldehyde 2 mL
d. 2-pentanon
e. formalin 2 mL
f. isopropyl alcohol enough
g. ethanol enough
h. benedict reagent 20mL
i. Sodium hydroxide solution 1% 1mL
j. Sodium hydroxide solution 3% 14 drops
k. cyclohexanol 2 mL
l. AgNO3 solution 1% enough
m. Sodium bisulphite 5 mL
n. HCl some drops
o. Hydroxamine hydrochloride enough
p. Phenylhydrazyne reagent 7,5 mL
q. Methanol enough
r. 2-pentanone
s. Iodium Solution 40 mL
t. Iu water enough
u. 2,4 diprophyl hydrazine enough
v. KMnO4 1 N 3 mL
w. FeCl3 5% 3 mL
x. K4FeCN6 few drops
y. H2SO4 concentrated enough
z. Acetaldehyde

F. Lanes work :
1. Tollens Reagent Preparation
2 mL of AgNO3 1 %

Poured into clean test tube


Added 1 mL of NaOH 5%
Shake it

Precipitate

Added some drops of NH4OH


Shaken until precipitate dissolved

Tollens Reagent

Reaction : 2 AgNO3 (aq) + 2 NaOH(aq) → Ag2O (s) + NaNO2 (aq) + H2O (l)

Ag2O (s) + NH4OH (aq) → 2Ag(NH3)2OH (aq)

Test Tube 1 :
O

H3C C H + 2Ag(NH ) OH (aq) →


3 2
O

H3C C OH + 2Ag (s) + 3NH (aq) + H O (l)


3 2
Test Tube 2:
O

H3C C CH3 (aq) + 2Ag(NH ) OH (aq) →


3 2
Test tube 3 :
O

(aq) + 2Ag(NH3)2OH (aq) →

Test tube 4 :
O O

H C H (aq) + 2Ag(NH3)2OH (aq) → H C OH (aq) + 2Ag(s) + 2NH3 (aq) +


H2O (l)
Tollens Reagent

Distributed 1 mL into test tube

Reagent A Reagent B Reagent C Reagent D

Addded Addded Addded Addded


acetaldehyde acetone cyclohexanone formalin

Shaked and waited 10 minutes


Put the test tube into hot water
if there no reaction
Written the result

Result

2. Fehling Test Reagent


Fehling Reagent

Distributed 5 mL into test tube

Reagent A Reagent B Reagent C

Addded 2 ml of Addded 2 mL of Addded 2 mL of


formaldehyde acetone cyclohexanone

Placed into room temperature


Observed its change in 10-15
minutes

Result

Reactions:

2KNaC4H4O4 (aq) + 2Cu2+ (aq) + 2OH- → C4(C4H2O6)2(aq) + Cu(OH)2 + 2Na+ +2K+


+2H+

Test tube 1 :
O O

H C H (aq) + 2Cu2+ (aq) + 2OH- → H C H + Cu2O (s) + 3H2O(l)


Test tube 2:
O

H3C C CH3 (aq)+ 2Cu2+ (aq) + 4OH- →


Test tube 3:
O

(aq) 2Cu2+ (aq) + 5OH- →

3. Bisulphite Addition

Reactions:

OH O

O
H3C C S O Na

H3C C CH3 (aq) + NaHSO3 (aq) CH3 O (aq)

OH O
OH O

H3C C S OH
H3C C S O Na

CH3 O
(aq) + HCl (aq) CH3 O (aq) + NaCl (aq)
4. Testing with Phenylhidrazine

Reactions:
O

C H
H H
H2N N N N C
H
(aq) + (aq) (aq) + H2O (l)

H H
H2N N N N

(aq) + (aq) (aq) + H2O(l)

The melting point of phenylhydrazine benzaldehyde = 156oC


(Chemical book,2017)

The melting point of cyclohexanone phenylhidrazinone = 78-90oC


(P212121 company information, 2018)

5. Haloform Reaction
Reactions:

CH3COCH3 (aq) + 3I2 + 4OH- → 2CHI3 (aq) + CHCOO- (aq) + 3H2O (l) + 3I-
CH3CH(CH3)OH (aq) + 3I2 + 4OH- → CH3COOCH3(aq) + 3I2 + 4OH- (aq) → 2CHI3
(aq) + CH3COO- (aq) + 3H2O (l) + 3I-(aq)

6. Aldol condensation

Reactions :

H3C C H (aq) + OH-

O O O
O
H2
H3C C C C H
H3C C H (aq) + -H2C C H (aq) H (aq)
O O
O
H2 H3C C C C
H3C C C C H H H
H (aq) + H2O panas H (aq)

7. Carboxylic identifications

15 ml of formic acid

Poured into a test tube


Added 3 mL of KMnO4
Observed changes that occur

Result
Reactions:

3HCOOH + KMnO4 → 2K+ + 2MnO2↓ + H2O + 3CO2 ↑+ 2OH-

CH3COONa (aq) +FeCl3(aq) → (CH3COO)3Fe (s) + NaCl (s)

FeCl3 (aq) + K4FeCN6(aq) → KCl (aq) + Fe4[Fe(CN)6]3 (s)


G. Result of experiment :

No Lanes work Observation Result Reaction Conclusion


. Before After
1. a) Tollens Reagent 2 ml of AgNO3 = AgNO3 1% + 2 AgNO3 (aq) + 2 Acetaldehyde and
colourless NaOH 5% = light NaOH(aq) → Ag2O (s) + formalin react with
2 mL of AgNO3 1 % solution brown solution and NaNO2 (aq) + H2O (l) tollens formed silver
brown precipitation mirror but in our
Poured into clean test tube NaOH 5 % = Ag2O (s) + NH4OH (aq) experiment aldehyde
Added 1 mL of NaOH 5% colourless AgNO3 + NaOH + → 2Ag(NH3)2OH (aq) are not formed silver
Shake it solution NH4OH = mirror.
colourless solution Acetone and
Precipitate NH4OH 2% = sichlohexanon do
light brown not react with tollens
Added some drops of NH4OH soolution reagent.
Shaken until precipitate dissolved

Tollens Reagent Test Tube 1 :


O
b) Acetaldehide = Tollens +
Tollens Reagent colourless, acetaldhide = H3C C H +
purgentodor brownish
Distributed 1 mL into test tube 2Ag(NH3)2OH (aq) →
O
Acetone = Acetone+ tollens =
Reagent A Reagent B Reagent C Reagent D colourless colourless black
H3C C OH + 2Ag
Addded Addded Addded Addded prcipitate
acetaldehyde acetone cyclohexanone formalin cyclohexanon = (s) + 3NH3 (aq) + H2O (l)
colourless Cyclohexanone + Test Tube 2:
Shaked and waited 10 minutes tollens = darkgrey O
Put the test tube into hot water Formalin =
if there no reaction colourless Formalin + tollens H3C C CH3 (aq) +
Written the result
= black 2Ag(NH3)2OH (aq) →
Result
Test tube 3 :
O

(aq) +
2Ag(NH3)2OH (aq) →
Test tube 4 :
O

H C H (aq) +
2Ag(NH3)2OH (aq) →
O

H C OH (aq) +
2Ag(s) + 2NH3 (aq) +
H2O (l)
2. Fehling Reagent Test Fehling A = light Fehling A+ Fehling 2KNaC4H4O4 (aq) + Formaldehyde
blue colour B = blue solution 2Cu2+ (aq) + 2OH- → oxydized while
C4(C4H2O6)2(aq) + ketone do not react
Fehling B = Fehling A+ Fehling Cu(OH)2 + 2Na+ +2K+ with fehling.
colourless B + Formadehyde +2H+ Indicated by the
= formed of red
Formaldehydes = There are two layer Test tube 1 : precipitation on
colourless . O aldehyde solution.
Upper layer = dark
Acetone = green solution H C H (aq) +
colourless Lower layer = blue 2Cu2+ (aq) + 2OH- →
solution O
Cyclohexanon =
colourless Fehling A, B + H C H + Cu2O (s)
Acetone = there are
+ 3H2O(l)
two layer white and
Test tube 2:
black layer O

Fehling A, B +
H3C C CH3 (aq)+
cyclohexanon =
form two layer. 2Cu2+ (aq) + 4OH- →
White and blue Test tube 3:
O

(aq) 2Cu2+
(aq) + 5OH- →
3. Bisulphite Addition Sodium Sodium bisulphate O From our experment
bisulphate = + acetone = turbid addition
turbid solution solution H3C C CH3 (aq) + nuchleophilic
(prescipitate and NaHSO3 (aq) reaction indicated by
Acetone = filtrate) the physical changes
colourless OH O from white turbid
Sodium bisulphate colourless solution.
+ acetone + ethanol H3C C S O Na
= turbid solution
CH3 O

Residue = white (aq)


powder OH O

Residue + HCl H3C C S O Na


concentrated +
cooled = colorles CH3 O

solution (aq) + HCl (aq)


OH O

H3C C S OH

CH3 O
(aq) + NaCl (aq)
4. Testing with phenylhidrazine Phenilhydrazine = Phenylhidrazine + O Benzaldehid and
yellow solution benzaldehid= two cyclohexanone
C H
layers. Upper = formed osazion
Benzaldehide = white crystall when reacted
colourless Lower= orange (aq) with fenilhidrazin.
precipitate + The melting point of
Cyclohexanone= benzaldehyde > he
colourless Phenylhidrazine + H melting point of
H2N N
Ethanol = benzaldehid + cuyclohexanone
colourless filterred = orange
(aq)
residu The melting point of
H benzaldehyde =
N N C
Residue + water + H 144oC
ethanol = orange The melting point of
residu cyclohexanone =
(aq) + H2O (l)
98oC
Phenylhidrazine + O
cyclohexanol = two
layer. Upper=
yellow oily (aq) +
Lower= colourless
H
H2N N
Phenylhidrazine +
cyclohexanol + (aq)
filtered = yellow
residue

Residue + water + H
N N
ethanol = yellow
residue
(aq) + H2O(l)
Melting point of The melting point of
benzaldehyde = phenylhydrazine
144oC benzaldehyde = 156oC
(Chemical book,2017)
Melting point of
cyclohexanone = The melting point of
98oC cyclohexanone
phenylhidrazinone = 78-
90oC
(P212121 company
information, 2018)
5. Haloform Reaction NaOH = NaOH 5% + CH3COCH3 (aq) + 3I2 + From this
colourless acetone + I2= 4OH- → 2CHI3 (aq) + experiment, ktone
turbid CHCOO- (aq) + 3H2O (l) given positive result
Acetone = (precipitated) + 3I- when reacted with
colourless haloform. Indicated
NaOH 5% + CH3CH(CH3)OH (aq) + with turbid
Isopropyl alcohol isopropyl alcohol + 3I2 + 4OH- → precipitation.
= colourless iodium= colourless CH3COOCH3(aq) + 3I2
+ 4OH- (aq) → 2CHI3 On reaction between
Iodium = yellow (aq) + CH3COO- (aq) + NaOH and acetone
solution 3H2O (l) + 3I-(aq) resulting white
precipitate.

On reaction between
NaOH and isopropyl
alcohol resulting
colourless solution.
6. Aldol Condensation NaOH = NaOH + O Aldol condensation
colourless Acetaldehyde = is reaction between
yellow grenish H3C C H (aq) + aldehyde and base.
Acetaldehyde= solution OH- Indicated with the
colourless rancid smell and
NaOH + O colourless solution.
Acetaldehyde + but from our
boiled = orange experiment formed
H3C C H (aq)
solution orange solution
O
Smell = rancid
H3C C H (aq) +
O

-
H2C C H (aq)
O
O
H2
H3C C C C H
H
(aq)

O
O
H2
H3C C C C H
H
(aq) H2O panas
O

H3C C C C
H H
H
(aq)
7. Carboxylic Identification Formic acid = Formic acid + 3HCOOH + KMnO4 → Formic acid oxidized
colourless KMnO4 = brown 2K+ + 2MnO2↓ + H2O + by KMnO4 formed
15 ml of formic acid solution blackish solution 3CO2 ↑+ 2OH- MnO2 (black
precipitate)
Poured into a test tube KMnO4 = purple Formic acid +
Added 3 mL of KMnO4 solution KMnO4 + cooled in Carboxylic can be
room temperature = identified with
Observed changes that occur
colourless solution reacting CH3COONa
CH3COONa = and black solution 10% with
Result colourless precipitate FeCl3 5% resulting
filtrate that
FeCl3 = yellow CH3COONa + CH3COONa (aq) contained Ferri ion
solution FeCl3 = red +FeCl3(aq) →
solution (CH3COO)3Fe (s) + NaCl It can be proved by
K4FeCN6 = light (s) the colour
yellow CH3COONa + comparation
FeCl3 + heated FeCl3 (aq) + between FeCl3 and
filtrate = orange K4FeCN6(aq) → KCl (aq) the filtrate colour
solution + Fe4[Fe(CN)6]3 (s) that added with
K4FeCN6
Residue = dark red

Filtrate + K4FeCN6
= dark blue
H. Analysis And Explanation
The title of this experiment is aldehyde, ketone, and carboxylic Acid Idetification.
The purpose of this experiment is to identified the aldehyde group in organic compound,
to indentified the ketone group in organic compound, to identified the carboxylic group in
organic compound, to differentiate the aldehyde group, ketone group and carboxylic group
that in organic compound. The experiment already started and done at Tuesday, 6 March
2018.
On this experiment there are seven flow chart that is tollens reagent preparation,
fehling or benedict reagent, bisulphite addition, testing with phenylhydrazine, haloform
reactions, aldol condensation and carboxykic identification.
1) Tollens Test
The purpose of the first experiment “Tollens Test” is to identified and
differentiate organic compound contained aldehyde and ketones group. The principal
of tollens test is aldehyde oxidized form carboxylic acid meanwhile Ag+ ion reduced
form Ag metal identificated with silver mirror. On this experiement the tester are
acetaldehyde, acetone, siclohexanon, and formaldehyde.
The first step is cleaned all of the tools. Then colourless 2 ml of AgNO3
entered into clean test tube, then added colourless 1 ml of NaOH 5% and shaken it
then formed black precipitate. The purpose of NaOH 5% addition is to form salt of Ag.
Then added some drops of colourless NH4OH 2% drop by drop while shaken until it
resoluble, the function of NH4OH 2% addition is to give base condition and dissolved
silver salt that have been formed. The reaction are,
AgNO3 (aq) + 2NaOH (aq)  Ag2O (s) + NaNO3 (aq) + H2O (l)
Ag2O (s) + NH4OH (aq)  Ag(NH3)2OH (aq)
The next step are entered 1 ml of tollens reagent into test tube A, test tube B,
test tube C and test tube D that have been washed, dried into oven. The purpose is to
sterilized the tools. On A tube added colourless acetaldehyde solution and resulted
colourless solution. Then heated on steam bath for 5 minutes. Acetaldehyde oxidized
by tollens reagent, indicated by the silver mirror formation. But from our experiment
the reaction between acetaldehyde and tollens reagent do not formed silver mirror. The
reason are there is impurities on test tube and the materials that have been used are
broken. From our experiment the result is yellow solution with brown precipitate. The
reaction are,

. On B tube added 2 ml colourless acetone solution, shaken, resided it for 10


minutes and resulted yellow solution. Then heated on steam bath for 5 minutes, there
is no colour changing. Siclohexanone does not react with tollens reagent. Based on
theory siclohexanone does not react by tollens reagent and this experiment proved that
there is no reaction occurs, indicated by no silver mirror are formed.
C3H6O (aq) + 2Ag(NH3)2OH (aq)  no reaction
On C tube added 2 ml colourless cyclohexanone solution, shaken, resided it for
10 minutes and resulted dark grey solution with black precipitate. Then heated on
steam bath for 5 minutes, there is no colour changing. Siclohexanone does not react
with tollens reagent. Based on theory siclohexanone does not react by tollens reagent
and this experiment proved that there is no reaction occurs, indicated by no silver
mirror are formed.

(ag) + 2Ag(NH3)2OH (aq)  no reaction

On D tube added colourless formalin solution and resulted colourless solution.


Then heated on steam bath for 5 minutes. Formalin oxidized by tollens reagent,
indicated by the silver mirror formation. But from our experiment the reaction between
formalin and tollens reagent do not formed silver mirror. The reason are there is
impurities on test tube and the materials that have been used are broken. From our
experiment the result is black solution with black precipitate. The reaction are,

(ag) + 2Ag(NH3)2OH (aq) →


(aq) + 2Ag(s) + 3NH3(aq) + H2O (l)
2) Fehling or Benedict Reagent Test
The second experiment was testing the aldehyde or ketone substance with
Fehling or Benedict. Firstly, 10 mL Fehling A and Fehling B is mixed into flask. And
took 5 mL of its mixture and divided into 4 tubes. The first tube is added with 2 mL
formaldehyde. The second tube is added with 2mL acetone. The third tube is added
with 2mL cyclohexanone. After that all of the tube are putted into cold water and
observed the changers for 10-15 minutes.
After reaction process finish, the changers that happens are: for the first tube,
it formed 2 layers solution. The upper layer has dark green color, the lower layer has
blue color.

O O

H C H (aq) + 2Cu2+ (aq) + 2OH- → H C H + Cu2O (s) + 3H2O(l)

For the second tube, it also formed 2 layers, but it has different color, the colors
are white for the upper layer, and blue for the lower layer.

H3C C CH3 (aq) + 2Cu2+ (aq) + 4OH- →


The third tube it also formed two layers, the color that forms are white for the
upper layer and blue for the lower layer.
O

(aq) 2Cu2+ (aq) + 5OH- →

Formaldehyde oxydized while ketone do not react with fehling. Indicated by


the formed of red precipitation on aldehyde solution.
3) Bisulphite Addition

From our experment addition nuchleophilic reaction indicated by the physical


changes from white turbid colourless solution.

4) Testing with Phenylhydrazine


The fourth experiment was testing with phenylhydrazine which aims to identify
organic compounds containing aldehyde groups and those containing ketone groups.
In addition, in this experiment also determine the melting point of both. Initially
prepared two test tubes each of which were included 2.5 ml of colorless
phenylhydrazine.
On the first tube 10 drops of colorless benzaldehid are added. When added with
benzaldehid the solution is yellow faded and precipitated. After that, the tube is shaken
strongly for 1-2 minutes until it blends. The function of shaking is to allow quicker
precipitation to form. In this case, the solution becomes white with orange precipitate.
After that, the solution is filtered by using a filter paper which results in a residue of
orange precipitate with a colorless filtrate. After that, the residue is washed with cold
water and ethanol sufficiently. The function of the addition of water is to remove any
residual filtrate remaining on the residue. While the addition of ethanol aims to re-
melt. After washing with ethanol, the colored deposits are more orange and clot. After
that, the precipitate is inserted into a desiccator flask that aims to dry the sediment in
order to test its melting point. This residue drying process takes 2 days. After drying,
the residue is tested its melting point. When it is dry, the residue changes color to
brownish. When tested the melting point of the residue the result is 144 ° C.
Based on the melting point theory of pheylhydrazine benzaldehid is 156˚C. the
cause of the experimental melting point lower than the theory is that because there is
still a filtrate on the residue, the pheylhydrazine benzaldehid residue has not been
completely dry at the time of the melting point test. The reaction are,
Thereafter on a second tube containing 2.5 ml of a colorless phenylhydrazine
solution. Added 10 drops of colorless cyclohexanone. When added with brown
cyclohexanone the solution is formed of precipitate. After that, the tube is shaken
strongly for 1-2 minutes until it blends. The function of shaking is to allow quicker
precipitation to form. After shaking is formed two layers, the top layer is oily yellow,
while the bottom layer is colorless. Thereafter, the solution is filtered using filter funnel
resulting in a yellow sludge residue such as oil and a colorless filtrate. After that, the
residue is washed with cold water and ethanol sufficiently. The function of the addition
of water is to remove any residual filtrate remaining on the residue. While the addition
of ethanol aims to re-melt. After washing with ethanol, the precipitate changes color
to yellow. After that, the precipitate is inserted into a desiccator flask that aims to dry
the residue in order to test its melting point. This residue drying process takes 2 days.
After dry the residue changes color to brownish and clot. The residue is then tested for
the melting point. In this case, the melting point of the obtained residue is 98 ° C.
Based on the melting point theory of cyclohexanone phenylhydrazone is 80˚C.
The cause of the experimental melting point lower than the theory is that because there
is still a filtrate on the residue, the cyclohexanone phenylhydrazone residue has not
been completely dry at the time of the melting point test. The reaction are,
5) Haloform Reaction
From this experiment, ktone given positive result when reacted with
haloform. Indicated with turbid precipitation. On reaction between NaOH and
acetone resulting white precipitate. On reaction between NaOH and isopropyl
alcohol resulting colourless solution.
CH3COCH3 (aq) + 3I2 + 4OH- → 2CHI3 (aq) + CHCOO- (aq) + 3H2O (l) + 3I-
CH3CH(CH3)OH (aq) + 3I2 + 4OH- → CH3COOCH3(aq) + 3I2 + 4OH- (aq) →
2CHI3 (aq) + CH3COO- (aq) + 3H2O (l) + 3I-(aq)
6) Aldol condensation
The sixth experiment of aldol condensation aims to observe the changes that
occur when strong bases are added to the aldehyde group. The principle of this
experiment is that the aldehyde group will condense with each other after reacting with
aqueous base solution and producing an aldol which, when heated, will remove water
to produce unsaturated aldehydes, ie, crotonaldehyde. The first is 4 ml of a colorless
5% NaOH solution was inserted into the reaction tube and then added 0.5 mL of
colorless and characteristic odorless acetaldehyde, well shaken to homogeneous and
produced a yellow solution with a strong odor. The solution is then boiled in a water
bath for 3 minutes and produces an orange solution with a rancid odor. The reaction
are,
7. Carboxylic Identification
Formic acid oxidized by KMnO4 formed MnO2 (black precipitate). Carboxylic
can be identified with reacting CH3COONa solution 10% with FeCl3 5% resulting
filtrate that contained Ferri ion. It can be proved by the colour comparation between
FeCl3 and the filtrate colour that added with K4FeCN6.
I. Discussion

The first experiment is Testing aldehyde and ketones group with tollens reagent.
The tube A is reaction between acetaldehyde and tollens reagent. The tube D is the reaction
between foemalin and tollens reagent. Our experiment unappropriate with the teory
because of there were impurities on test tube and the materials that have been used are
broken.

The fourth experiment is phenylhydrazine which aims to identify organic


compounds containing aldehyde groups and those containing ketone groups. Based on
theory the melting point of pheylhydrazine benzaldehid and cyclohexanone
phenylhydrazone are 156˚C and 80˚C. our experiment are unappropriate with the teory
because of there were impurities on test tube and the materials that have been used are
broken.

J. Conclusion
1. Acetaldehyde and formalin react with tollens formed silver mirror but from our on
acetaldehyde and formalin are not formed silver mirror. Acetone and cyclohexanone
do not react with tollens reagent.
2. Formaldehyde oxydized while ketone do not react with fehling. Indicated by the
formed of red precipitation on aldehyde solution.
3. From our experment addition nuchleophilic reaction indicated by the physical changes
from white turbid colourless solution.
4. From our experiment on benzaldehyde and cyclohexanone are formed osazon crystal
when reacted with phenylhydrazin. The melting point of benzaldehyde is higher than
the melting point of cyclohexanone. The melting point of pheylhydrazine benzaldehid
is 144˚C and the melting point of cyclohexanone phenylhydrazon is 98˚C.

5. From this experiment, ktone given positive result when reacted with haloform.
Indicated with turbid precipitation. On reaction between NaOH and acetone resulting
white precipitate. On reaction between NaOH and isopropyl alcohol resulting
colourless solution.

6. Aldol condensation is reaction between aldehyde and base. Indicated by rancid smell
and colourless solution. But from our experiment formed orange solution.
7. Formic acid oxidized by KMnO4 formed MnO2 (black precipitate). Carboxylic can be
identified with reacting CH3COONa solution 10% with FeCl3 5% resulting filtrate that
contained Ferri ion. It can be proved by the colour comparation between FeCl3 and the
filtrate colour that added with K4FeCN6
K. References
Carey, Franciss A. 1937. Organic Chemistry sevent edition (e-book). Virginia :
University of Virginia
McMurry, John. 2008. Organic Chemistry seventh edition. USA : Thomson Higher
Education
Wade JR, LG. 2013. Organic Chemistry eight edition (e-book). USA : United States of
America.
Tim Kimia Organik. 2017. Petunjuk Praktikum Kimia Organik. Surabaya : Universitas
Negeri Surabaya
L. Attachment
No. PICTURES NO PICTURES
1. AgNO3 + NAOH 5% 2. TOLLENS REAGENT

3. Reagent A tollens 4. Tollens test (Tube B)

5. Tollens test (Tube C) 6. Tollens (Tube D)


7. Fehling + (Formaldehyde; acetone; 8. Bisulphite + Acetone + Ethanol
cyclohexanone)

9. Bisulphite addition filtrated 10. Filtrate of bisulphite addition

11. Residue of bisulphite addition 12. Residue + HCl


13. Benzaldehyde + Phenilhidrazin 14. Phenilhidrazin + Siclohexanone

15, 16. Haloform reaction (acetone,


isopropyl alcohol)
Benzaldehyde + Cyclohexanone
filtrated

17. Wet benzaldehid 18. Wet cyclohexanone


19. NaOH + Asetaldehid 20. NaOH + Asetaldehid + Heated

21. Asam Formiat + KMnSO4 22. CH3COONa + FeCl3

23. Filtrate Of Carboxylic Acid 24. Dry Benzaldehid


25. Melting Point Of Benzaldehid 26. Melting Point Of Cyclohexanone

27. Temperature Of Benzaldehid 28. Temperature Of Cyclohexanon