Aldehydes and Ketones Individual Laboratory Report

LBYCH63, EA2, Group # 5
Experiment #8: Aldehydes and Ketones

Razote, Bernard Jomari B.
Instructor: Sir Glenn Tan
Date Performed: November 11, 2014
Date Submitted: November 25, 2014
Abstract
A qualitative analysis of aldehydes and ketones was conducted in the experiment. Four test samples,
namely acetone, formaldehyde, benzaldehyde, and cyclohexanone, were used in the experiment. Various
parameters regarding the physical properties of aldehydes and ketones were determined using tests such as the
oxidation with potassium permanganate, 2,4-dinitrophenylhydrazine test, Schiffs test, Tollens test, Fehlings test,
iodoform test, reactions with sodium bisulfite, and the chromic acid test. The objectives of the experiment were
met since the physical properties of the aldehydes and ketones were observed using the tests. However, some
experimental results deviated from the theoretical one, such as the non-oxidation of formaldehyde with potassium
permanganate, and the negative results for the reactions of formaldehyde and acetone with sodium bisulfite.
These unforeseen errors and deviations in the result of the experiment can be attributed to the impurities that may
have altered the original result. The experiment would be very helpful in establishing the identity of a certain
unknown compound; however, additional tests such as Benedicts test and ceric nitrate test are recommended to
better establish the certainty of the unknown compound.
I.
Potassium permanganate is a strong oxidizing

agent used to test the presence of an aldehyde or a
ketone.
Introduction
Ketones and aldehydes are somewhat similar in

their structure, due to the presence of the carbonyl
group (C=O) in both of the compounds. However,
the two behave differently, due to the difference of
the attached groups in the carbonyl group. (1)
The main objective of the experiment is to
analyze qualitatively aldehydes and ketones through
the use of various tests. These tests include using
potassium permanganate to observe the oxidations
of aldehydes, using 2,4-dinitrophenylhydrazine to
determine the presence of an aldehyde or a ketone,
determining the presence of an aldehyde using
Schiffs , Tollens, and chromic acid test, using
Fehlings test to distinguish aromatic aldehydes from
aliphatic aldehydes, determining the presence of
methyl ketones through the appearance of iodoform,
and using sodium bisulfite in determining the
presence of an aldehyde or an aliphatic methyl
ketone.
The significance of the experiment is to establish
the identity of a certain compound, and to determine
whether it is an aldehyde or a ketone. The
experiment is also significant in determining the
identity of an unknown compound, which can be
unfolded using the various tests in the experiment.
A. Oxidation of
Permanganate
Aldehydes
Aldehydes and Ketones
with
If the compound present is an aldehyde, it will

be readily oxidized by the potassium permanganate
into a carboxylic acid due to the presence of the
hydrogen atom bonded to the carbonyl group. Since
7+
the reaction is a redox reaction, Mn will be reduced
4+
4+
to Mn . Mn
is present in the solution as
manganese dioxide, which gives the solution a
brown color. The presence of the brown color is
regarded as the positive result for the experiment.
(2)
+ MnO2
Figure 1.1 Reaction of Aldehydes with KMnO4 (Oxidation of
aldehydes and ketones, n.d.)
If the compound present is a ketone, it is

generally not oxidized by potassium permanganate,
unless in extreme conditions such as the presence
of heat. If KMnO4 is able to oxidize the ketone, a
cleavage mixture of two carboxylic acids would be
present in the solution. (3)
Potassium
Page 1 of 12
Figure 1.2 Reaction of Ketones with KMnO4 Oxidation of

aldehydes and ketones, n.d.)
However, ketones with benzylic carbonyl groups

can be easily oxidized by KMnO4. (4) This is
because the permanganate adds itself to the double
bond in the enol form of the ketone. The end product
of the reaction would be a dicarboxylic acid. (5)
The appearance of a magenta color in the

solution is regarded as the positive result for the
Schiffs Test. This positive result is expected for
aldehydes. (9)
B. 2,4-Dinitrophenylhydrazine Test with Aldehydes

and Ketones
The 2,4-dinitrophenylhydrazine is a compound
with a hydrazine (H2N-NH2) attached to the first
carbon of a benzene ring, and two nitro groups
(NO2) attached to the second and fourth carbon,
respectively. Due to its sensitivity to shock and heat,
it is usually dissolved in water to avoid any violent
explosion. (6)
The test of 2,4-dinitrophenylhydrazine is a tool
used to verify if a certain compound is an aldehyde
or a ketone. The appearance of a yellow to orange
precipitate indicates a positive result.
When an aldehyde is dropped into the solution
containing 2,4-dinitrophenylhydrazine, it forms
aldehyde
2,4-dinitrophenylhydrazone,
which
precipitates out in the solution as a yellow to orange
solid. (7)
Figure 1.5 Reaction of Aldehydes with Bisulfite Ion (Identification

of an Unknown Alcohols, Aldehydes, and Ketones, n.d).
For ketones, no color change is expected to

happen. A possible color change, although not the
same as magenta, is also possible to happen
D. Tollens Test for Aldehydes
The Tollens Test is another useful tool in
distinguishing aldehydes from ketones. It is prepared
by mixing silver nitrate and sodium hydroxide, and
adding ammonium hydroxide to remove the red
precipitate and make the solution colorless.
However, it is not usually done in the laboratory due
to its explosive character, and health risks due to the
production of silver upon the completion of the
experiment. (9)
For the Tollens Test, the formation of a solid
silver precipitate is regarded as a positive result.
Figure 1.3 Reaction of Aldehydes with 2,4-Dinitrophenylhydrazine

(Addition-elimination reactions of aldehydes and ketones, 2004)
Likewise, when a ketone is dropped into a

solution containing 2,4-dinitrophenylhydrazine, it
forms ketone 2,4-dinitrophenylhydrazone, which
precipitates out in the solution also as a yellow to
orange solid. (7)
Figure 1.4 Reaction of Ketones with 2,4-Dinitrophenylhydrazine

(Addition-elimination reactions of aldehydes and ketones, 2004)
C. Schiffs Test for Aldehydes

Schiffs Test is done in order to distinguish an
aldehyde from a ketone. The solution to be used, the
Schiffs reagent, is produced by the reaction of a dye
such as pararosaniline with sodium bisulfite. (8)
When an aldehyde is placed into a test tube

containing Tollens reagent, a silver mirror is
produced. (9)
Figure 1.6 Reaction of Aldehydes with Tollens Reagent

(Reactions of aldehydes, ketones and phenols, 2011).
However, when a ketone is placed into the test

tube containing Tollens reagent, no precipitate
would form, since no reaction will happen. (9)
E. Fehlings Test for Distinguishing
Aldehydes from Aliphatic Aldehydes
Aromatic
Page 2 of 12
Fehlings Test is done to distinguish aliphatic

aldehydes from aromatic aldehydes. Fehlings
Solution A is prepared by adding a few drops of
concentrated sulfuric acid to an aqueous solution of
copper sulfate pentahydrate. On the other hand,
Fehlings Solution B is prepared by mixing sodium
hydroxide with potassium sodium tartrate. (10)
A positive result for the Fehlings Test is the
appearance of a red precipitate, cuprous oxide,
which happens when there is a presence of an
aliphatic aldehyde. (11)
Figure 1.8 Reaction of Methyl Ketones to NaOH-I2-KI Solution in

Iodoform Test (Triiodomethane reacted with methyl ketones,
2004)
The iodoform test is also applicable to alcohols

having RCH3CHOH. If an alcohol has such structure,
the yellow precipitate, iodoform, can also be formed.
The same reaction mechanism happens for alcohols
having the said structure with methyl ketones. (12)
G. Reaction with Sodium Bisulfite for Aldehydes
and Aliphatic Methyl Ketones
Sodium Bisulfite Test is used to determine if an
unknown compound is an aldehyde or an aliphatic
methyl ketone. If the unknown substance is either of
the two aforementioned, a white precipitate is
formed.
Figure 1.7 Reaction of Aldehydes with Fehlings Reagent

Due to the nucleophilic nature of the bisulfite ion,

it attacks the aldehyde or methyl ketone by breaking
the bond of the carbon-oxygen double bond. The
bisulfite ion then attaches itself to the original
carbonyl carbon to form the bisulfite addition
compound. (13)
On the other hand, aromatic aldehydes and

ketones give a negative result to Fehlings test,
since no red precipitate would appear after being
added to the Fehlings solution.
F. Iodoform Test for Methyl Ketones
The iodoform test is used to distinguish a methyl
ketone from other ketones and aldehydes. The
presence of iodoform, a yellow precipitate, is the
indication that the substance is a methyl ketone. (12)
In basic conditions, the alpha proton, which is
next to the carbon, is removed. The removal of the
alpha proton causes the -carbon to be nucleophilic,
which enables it to attack an iodine molecule. The
presence of the iodine in the -carbon makes the
two other hydrogens more acidic, therefore the two
hydrogens get attacked by the nucleophilic base
until all of them are replaced by the iodine. After
that, the bond between carbonyl carbon and the
carbon containing the iodine molecules will break,
forming an acid salt and iodoform, a yellow
precipitate. (9)
Figure 1.9 Reaction of Sodium Bisulfite with Aldehydes

The presence of larger groups in a ketone

sterically hinders the bisulfite ion in attaching itself to
the carbonyl carbon. Hence, for ketones with large
bulky groups would not form the bisulfite addition
compound; only methyl ketones have the capability
of being attached by the bisulfite ion since the
presence of the methyl group would not affect that
much in the attachment of the bisulfite ion to the
carbonyl carbon. (13)
Figure 1.10 Reaction of Propanone, a Ketone, with Sodium

Bisulfite
(Simple addition to aldehydes and ketones, 2004).
H. Chromic Acid Test for Aldehydes

Chromic Test is done to distinguish an aldehyde
from a ketone. Since chromic acid is a strong
oxidizer, it can easily oxidize an aldehyde into a
carboxylic acid. This oxidation reaction results to the
Page 3 of 12

6+
3+
3+
reduction of Cr ions into Cr . The presence of Cr

is seen in chromous sulftate, Cr2(SO4)3, which is
responsible for the green color. The green color
symbolizes that the aldehyde is oxidized. (14)
3RCHO + 2CrO3 + H2SO4 3RCOOH +
Cr2(SO4)3 + 4 H2O
On the other hand, due to stability, ketones tend
to resist any reactions with oxidizing agents such as
chromic acid. Hence, no discoloration of the reagent
would happen in the presence of a ketone.
II.
Experimental Procedure
A. Oxidation of Aldehydes with
Permanganate
Potassium
One milliliter of distilled water was placed into

four test tubes. 5 drops of KMnO4 was added to
each test tube, and 4 drops of acetone,
benzaldehyde, formaldehyde and cyclohexanone
st
nd
rd
th
were placed into the 1 , 2 , 3 , and 4 test tube,
respectively.
For acetone, the purple solution turned faint red
upon addition. For benzaldehyde, the purple solution
turned light brown upon addition. For formaldehyde,
the purple solution turned red upon addition. For
cyclohexanone, the purple solution turned red upon
addition.
and Ketones
One milliliter of 2,4-dinitrophenylhydrazine was
placed into each of the four test tubes. Two drops of
benzaldehyde, cyclohexanone, formaldehyde and
st
nd
rd
th
acetone were placed into the 1 , 2 , 3 , and 4 test
tubes, respectively. All test tubes containing 2,4dinitrophenylhydrazine had an initial transparent
color.
For benzaldehyde, an appearance of an orange
precipitate was observed immediately after it was
dropped on the test tube. For cyclohexanone, an
appearance of a yellow precipitate was observed
immediately after it was dropped on the test tube.
For formaldehyde, an appearance also of a yellow
precipitate was observed in the test tube
immediately after it was dropped. Like formaldehyde
and cyclohexanone, acetone also yielded a yellow
precipitate after it was dropped on the test tube.
The
2,4-dinitrophenylhydrazine
test
was
repeated with ethanol and acetic acid. No
appearance of yellow to orange precipitate was
observed in both test tubes after they were dropped
into the 2,4-dinitrophenylhydrazine solution.

One milliliter of Schiffs reagent was placed into
each of the four test tubes. Four drops of acetone,
st
nd
rd
th
respectively. The test tubes were then swirled and
observed for appearance of a pink to purple
coloration.
For the first test tube, the original colorless
solution turned into red-orange upon addition of
acetone to the Schiffs reagent.
For the second test tube, the original colorless
solution turned into violet after addition of
benzaldehyde to the Schiffs reagent.
For the third test tube, the original colorless
solution turned into dark violet upon addition of
formaldehyde to the Schiffs reagent.
For the fourth test tube, the original colorless
solution turned into red-violet upon addition of
cyclohexanone to the Schiffs reagent.
The Tollens Test for Aldehydes was not
conducted in the laboratory due to the difficulty of
preparing the solution, since the solution should be
freshly prepared in order to avoid any explosion. In
addition, health concerns regarding the production of
the silver precipitate were taken into consideration to
avoid any hazardous effects. However, the
theoretical results of the experiment would be
explained in the Results and Discussion section.
Aromatic
One mL of Fehlings Solution A was mixed with

1 mL of Fehlings Solution B. Four mixtures of
Fehlings A and Fehlings B were then placed into
the four test tubes. Consequently, 4 drops of
formaldehyde, cyclohexanone, benzaldehyde and
st
nd
rd
th
acetone were placed into the 1 , 2 , 3 , and 4 test
tubes, respectively. Upon the addition of the test
samples, the test tubes were then submerged into a
hot water and were observed for the appearance of
a red precipitate. The original color of the solution
before the samples were placed is blue.
Page 4 of 12
For the test tube containing formaldehyde, a

blood red precipitate was observed after being
submerged into the hot water bath.
For cyclohexanone, no red precipitate was
formed after being submerged in the hot water bath
for about 5 minutes.
For the test tube containing benzaldehyde, no
red precipitate was formed also after being dipped in
hot water bath. Instead, a thin yellow-colored
immiscible layer was formed on top of the solution.
For acetone, no red precipitate also was formed
after being dipped in the hot water bath. Instead, an
immiscible layer was formed, with white layer on top
and blue layer at the bottom of the test tube.
The Fehlings Test was repeated using glucose
as the test sample. For the test tube containing
glucose, a red precipitate was formed after the test
tube was heated.
potassium iodide-iodine-sodium hydroxide mixture, a

cloudy yellow precipitate was formed.
G. Reactions with Sodium Bisulfite for Aldehydes
Four drops of acetone, benzaldehyde,
formaldehyde, and cyclohexanone were placed into
st
nd
rd
th
the 1 , 2 , 3 , and 4 test tube respectively. One
milliliter of sodium bisulfite solution was then placed.
Upon addition, the test tubes were shaken, and after
the shaking, the solution was let stand for 1 to 2
minutes. All of the test samples were transparent
before the addition of sodium bisulfite.
For acetone and benzaldehyde, the solution
remained transparent after addition of sodium
bisulfite. On the other hand, for benzaldehyde and
cyclohexanone, a colloidal precipitate was formed in
both of the test tubes after addition of sodium
bisulfite.
H. Chromic Acid Test for Aldehydes

Two milliliters of the reagent provided by the
technician, which is a combination of sodium
hydroxide and iodine-potassium iodide solution, was
placed into four test tubes. Four drops of acetone,
st
nd
rd
th
respectively.
Immediately, upon the addition of acetone to the
mixture of sodium hydroxide and iodine-potassium
iodide, a creamy whitish yellow precipitate was
observed.
When benzaldehyde was added to the mixture
of sodium hydroxide and iodine-potassium iodide, a
cloudy yellow bubble formation was observed. After
some time, the solution turned to cloudy white.
For formaldehyde, the solution stayed clear
when added to the mixture of iodine-potassium
iodide and sodium hydroxide.
The addition of cyclohexanone to the mixture of
iodine-potassium iodide and sodium hydroxide
produced a cloudy with yellow bubbles solution.
Similar as that of benzaldehyde, the solution turned
cloudy white after some time.
The iodoform test was repeated using isopropyl
alcohol as the test sample. Upon addition to the
One milliliter of acetone was placed inside a test

tube. 5 drops of chromic acid were then added to
acetone, and was observed for any reaction.
When no reaction was recorded after three
minutes of observation, one milliliter of acetone was
placed into four test tubes. 5 drops of chromic acid
were placed into each test tube, and 2 drops of
acetone,
benzaldehyde,
formaldehyde,
and
st
nd
rd
cyclohexanone were placed into the 1 , 2 , 3 , and
th
4 respectively. The test tubes were then shook and
observed for color change. The original color of the
solution before the test samples were dropped is
yellow.
For acetone, the solution remained yellow after
the addition of the test sample.
For both benzaldehyde and cyclohexanone, the
solution turned dark yellow upon the addition of the
test sample to their respective test tubes.
For formaldehyde, the solution turned light blue
green upon the addition of the test sample.
III.
Results and Discussion
A. Oxidation of
Permanganate
Aldehydes
with
Potassium
Page 5 of 12
Theoretically, formaldehyde, benzaldehyde and

cyclohexanone would positive results, since they
would be oxidized by potassium permanganate to
form brown manganese dioxide. On the other hand,
acetone is not expected to produce a positive result
for potassium permanganate.
Upon experimentation, acetone produced the
expected negative result, since a faint red color was
produced instead as brown. The absence of
manganese dioxide, which gives the brown color,
can be attributed to the inability of potassium
permanganate to completely oxidize acetone. Since
acetone is stable (since it has properties of a
ketone), it has a tendency to resist oxidation, that is
why no manganese dioxide appeared. The red to
purple color change can be attributed to another
unforeseen reaction of acetone with potassium
permanganate.
CH3COCH3 + KMnO4 No reaction
Benzaldehyde was able to produce the expected
positive result in the experiment; a light brown color,
which signifies the presence of manganese dioxide,
appeared in the test tube. Being a strong oxidizer,
potassium permanganate was able to convert
benzaldehyde into benzoic acid. On the other hand,
7+
4+
benzaldehyde reduced Mn into Mn , which gave
rise to the formation of brown manganese dioxide.
5C6H6CHO + 2KMnO4 + 6H 5C6H6COOH +
2+
+
2Mn + 3H2O + 2K
HCHO + MnO4 No reaction

-

and Ketones
For benzaldehyde, an orange precipitate
was expected to be observed. Acetone,
cyclohexanone and formaldehyde were expected to
have the formation of a yellow precipitate upon
addition to 2,4-dinitrophenylhydrazine. On the other
hand, for the ethanol and acetic acid, no precipitate
was expected to be observed when dropped in the
solution containing 2,4-dinitrophenylhydrazine.
Upon
experimentation,
benzaldehyde
produced a positive result for the 2,4Dinitrophenylhydrazine Test, since there was a
formation of an orange precipitate in the test tube.
The orange precipitate, benzaldehyde 2,4dinitrophenylhydrazone, was produced from the
reaction:
Cyclohexanone was also able to produce a

positive result for the experiment, due to the sepia
coloration upon addition. Since the permanganate
ion was able to attach itself to the enol form of
cyclohexanone,
it
was
able
to
oxidize
cyclohexanone into adipic acid. Hence, it resulted to
7+
4+
the reduction of Mn into Mn , which is the reason
why a sepia coloration was formed.
Figure 3.1 Reaction of Benzaldehyde with 2,4Dinitrophenylhydrazine
Cyclohexanone also produced a positive

result for the 2,4-Dinitrophenylhydrazine Test. The
yellow
precipitate,
cyclohexanone
2,4dinitrophenylhydrazone, was formed from the
reaction:
2C6H10O + 3MnO4 2C6H10O4 + 3MnO2

-
Formaldehyde, theoretically, must produce a

positive result for the experiment. This is because
formaldehyde will be oxidized into formic acid, which
7+
will result in the reduction on Mn . However, for the
experiment, a negative result was recorded, since
no brown color was seen which would indicate the
presence of manganese dioxide. This non-reaction
of formaldehyde can be attributed to the absence of
a basic medium such as sodium hydroxide that can
help in the reaction of formaldehyde with potassium
permanganate.
Figure 3.2 Reaction of Cyclohexanone with 2,4Dinitrophenylhydrazine
An appearance of a yellow precipitate, which

is an indication of a positive result, was also
observed in the addition of formaldehyde to the test
tube containing 2,4-dinitrophenylhydrazine. The
Page 6 of 12
precipitate,
formaldehyde
dinitrophenylhydrazone, was formed
reaction:
from
2,4the
Figure 3.3 Reaction of Formaldehyde with 2,4Dinitrophenylhydrazine
Acetone also produced a positive result, as

indicated by the formation of a yellow precipitate.
The precipitate, acetone 2,4-dinitrophenylhydrazone,
was formed from the reaction:
when added to the solution containing 2,4dinitrophenylhydrazine. On the other hand,

compounds that do not contain a conjugated
carbonyl group produce a yellow phenylhydrazone
derivative. This is the reason why a compound that
contained a conjugated carbonyl group like
benzaldehyde produced an orange phenylhydrazone
derivative, while the compounds that did not contain
a
conjugated
carbonyl
group
such
as
cyclohexanone,
acetone
and
formaldehyde
produced a yellow phenylhydrazone derivative. (15)
For ethanol, a negative result was observed
since no yellow to orange precipitate was observed.
This is because no reaction took place between the
two compounds.
No reaction
Also, for acetic acid, a negative result was

observed since no yellow to orange precipitate was
observed. This is because no reaction between the
compounds took place.
No reaction
Figure 3.4 Reaction of Acetone with 2,4-Dinitrophenylhydrazine
Due to the nucleophilicity of 2,4dinitrophenylhydrazine, it attacked the electrophilic

aldehyde and ketone compounds by bonding the
terminal nitrogen in the amino group to the carbonoxygen double bond, forming an intermediate
compound. However, since the reaction of 2,4dinitrophenylhydrazine with the aldehyde and ketone
is a nucleophilic addition-elimination reaction (or in
general terms condensation reaction), both the
oxygen in double bond with the carbon as well as
the hydrogen atoms bonded to the terminal amino
group were displaced, which gave rise to the
formation of the yellow or orange precipitate, a
phenylhydrazone derivative. (7)
The difference of the color phenylhydrazone
derivative depended on whether the compound
being tested contained a conjugate carbonyl group.
A compound containing a conjugated carbonyl group
has double bond that is separated only to the
carbonyl group by one single bond only, and
produces an orange phenylhydrazone derivative
No precipitate was observed when the two

compounds
were
placed
in
2,4dinitrophenylhydrazine because, in both of these
compounds, the electrons are more delocalized.
This delocalization of electrons enables them to
have various resonance structures which add to the
stability of the certain compound. Hence, the stability
of the compound resists the reaction of the acetic
acid and ethanol with 2,4-dinitrophenylhydrazine,
which is the reason why no precipitate was formed
for both ethanol and acetic acid. (16)
Theoretically, benzaldehyde and formaldehyde
should produce a positive result. On the other hand,
acetone and cyclohexanone were not expected to
produce the magenta color which signifies positive
results.
Upon experimentation, acetone produced a
negative result for the Schiffs reagent, because the
carbonyl group in acetone was sterically hindered.
This is due to the bulky methyl groups that surround
the carbonyl group. Hence, the bisulfite ion cannot
bond firmly into the acetone, which resulted to
another color change. The different color produced
Page 7 of 12
is a possible indicator that some of the acetone

molecules were able to bond with some of the
bisulfite ions but were not enough to give a positive
result. (15)
Figure 3.8 Reaction of Cyclohexanone with Bisulfite Ion

Theoretically, benzaldehyde will produce a
positive result for Tollens Test. It is because when
benzaldehyde is placed inside the test tube
containing Tollens reagent, a silver mirror would be
produced. This formation of precipitate is due to the
reaction:
Figure 3.5 Reaction of Acetone with Bisulfite Ion
Benzaldehyde and formaldehyde produced

positive results for the Schiffs reagent since the
carbonyl group in both of the compounds was not
sterically hindered. This is because the hydrogen
atom bonded to the carbonyl group was small; it
allowed the bisulfite ion to bond into the carbonyl
group, which resulted to the bisulfite addition
complex that produced the violet to dark violet color.
Figure 3.9 Reaction of Benzaldehyde with Tollens Reagent
Formaldehyde will also produce a positive result

for Tollens Test, since a silver mirror would be
produced if placed in the test tube containing
Tollens reagent. The formation of the solid silver
precipitate is governed by the reaction:
Figure 3.6 Reaction of Benzaldehyde with Bisulfite Ion
Figure 3.10 Reaction of Formaldehyde with Tollens Reagent
Figure 3.7 Reaction of Formaldehyde with Bisulfite Ion
Contrary to what was expected, cyclohexanone

produced a positive result in the Schiffs Test. This
was possible because, even though the carbonyl
group present in cyclohexanone is sterically
hindered due to the presence of the phenyl group,
the bisulfite ion was still able to attack
cyclohexanone by forming a bond in the carbonyl
group. Hence, it resulted to the formation of the
bisulfite addition complex which produced the redviolet color.
On the other hand, cyclohexanone would

produce theoretically a negative result, because no
silver precipitate would be formed for the Tollens
Test. This is because no reaction would happen to
facilitate the formation of the silver precipitate.
No reaction
Same with cyclohexanone, acetone would also

produce theoretically a negative result, because no
silver precipitate would be formed for the Tollens
Test. This is again due to the fact that no reaction
Page 8 of 12
would happen between acetone and the aqueous

diamminesilver(I) complex.
2C6H6CHO + NaOH C6H6CH2OH +
C6H6COONa
No reaction
Both of the aldehydes would produce a

silver mirror upon the addition to Tollens reagent.
This is because aldehydes are easily oxidized by the
Tollens reagent, due to the attached hydrogen to
the
carbonyl-containing
carbon.
Therefore,
aldehydes can reduce easily the silver present in the
+
0
Tollens reagent (Ag ) to the solid silver metal (Ag )
through redox reaction. This is the reason why upon
addition to Tollens reagent, formaldehyde and
benzaldehyde was able to produce a silver mirror.
On the other hand, ketones would not be
able to produce a silver mirror upon addition to
Tollens reagent. It is because unlike aldehydes,
ketones are not easily oxidized by the Tollens
reagent due to the lack of hydrogen attached to the
carbonyl-containing carbon. With the exception of
alpha-hydroxy ketones or acyloins, no reaction
would proceed from the test tubes containing
ketones like cyclohexanone and acetone that is why
no silver mirror would be formed. (17)
No reaction
For acetone, a negative result was also

recorded, since no red precipitate was observed.
Similar to that of cyclohexanone, acetone did not
react with the Fehlings solution that is why no
precipitate was formed.
No reaction
For glucose, a positive result was observed,

because a red precipitate was seen in the test tube.
The reaction of glucose with Fehlings solution is
represented by the reaction below.
Aromatic
For the experiment, formaldehyde and glucose

were expected to produce the red cuprous oxide
precipitate. On the other hand, benzaldehyde,
acetone, and cyclohexanone were not expected to
produce the red precipitate.
Formaldehyde produced a positive result on the
Fehlings Test, due to the formation of the red
precipitate. The precipitation of cuprous oxide from
formaldehyde is governed by the reaction
Figure 3.11 Reaction of Formaldehyde with Fehlings Reagent
Benzaldehyde produced a negative result for the

Fehlings test, because of the absence of the red
precipitate. The reaction of benzaldehyde with
Fehlings solution is represented by the reaction
below.
Cyclohexanone also produced a negative result

for the Fehlings test due to the absence of the
cuprous oxide precipitate. The reason for this is that
no reaction took place between cyclohexanone and
that of Fehlings solution.
Figure 3.13 Reaction of Glucose with Fehlings Reagent

(Carbohydrates, 2010)
Formaldehyde produced a positive result for the

Fehlings Test because it was oxidized by the
bistartatocuprate complex(II) into a carboxylate ion.
(10) This resulted to the reduction of copper(II) ions
into copper(I), which caused the formation of
cuprous oxide.
Benzaldehyde produced a negative result for the
Fehlings Test because upon addition to the
Fehlings solution, the benzaldehyde reacted to form
benzyl alcohol and sodium benzoate. This is due to
the presence of an alkali, which proceeded to
Cannizzaros Reaction instead of reducing the
copper(II) ions into copper(I) ions. (18) Hence, no
formation of cuprous oxide took place.
The yellowish immiscible layer formed on top of
the blue Fehlings solution upon the addition is
possibly due to impurities in the benzaldehyde
sample.
Page 9 of 12
Cyclohexanone and acetone produced a

negative result for the Fehlings Test because of the
2+
weak oxidizing nature of Cr complex. Ketones are
not easily oxidized due to their stability, and the
availability of a weak oxidizer would not facilitate in
the oxidation of the ketone. Hence, no precipitation
of cuprous oxide took place for both cyclohexanone
and acetone.
For glucose, a positive result was observed
because it contains an aliphatic aldehyde group,
which makes it a reducing sugar. (19) Since aliphatic
aldehydes are easier to be oxidized as compared to
aromatic aldehydes and ketones, the copper(II)
complex easily oxidized the aldehyde group in
glucose into its carboxylate ion. The oxidation of
glucose resulted to the reduction of the copper(II)
ions into copper(I) ions, which resulted to the
formation of the red precipitate cuprous oxide.
iodoform test, since

precipitate was seen.
no
formation
of
yellow
Although there was a carbon in one of the

attached groups (both for cyclohexanone), the
carbon-containing group present was a phenyl group
rather than a methyl group. Since iodine is a weak
oxidizing agent, it cannot oxidize phenyl groups,
which is the main reason why benzaldehyde and
cyclohexanone did not produce any yellow
precipitate.
Benzaldehyde:
+ I2 + OH
+ I2 + OH
No reaction
Cyclohexanone:
Acetone and isopropyl alcohol were expected to
produce positive results. On the other hand,
cyclohexanone, benzaldehyde and formaldehyde
were not expected to produce positive results.
Upon experimentation, acetone yielded a
positive result for the iodoform test, due to the
formation of the yellow precipitate. The presence of
the methyl group in one of the groups attached to
the carbonyl group is the reason why the iodoform
was formed upon the addition of acetone. The
expected result for acetone is a positive result.
No reaction
For isopropyl alcohol, a positive result was

recorded for the iodoform test even though it is an
alcohol. This is due to the presence of a methyl
group that contains the -carbon, which was
oxidized by the iodine to form the yellow precipitate,
iodoform.
+ 4I2 + OH
CHI3 + HCOONa + 8HI
Figure 3.13 Reaction of Acetone with KI-I2-NaOH Solution
For formaldehyde, a negative result was

recorded for the iodoform test, since no formation of
yellow precipitate was observed. This result can be
attributed to the absence of the methyl group that
contains the -carbon. Due to the lack of -carbon,
no attachment of iodine to carbon happened, which
resulted to the absence of the yellow precipitate.
+ I2 + OH
No reaction
In the experiment, both benzaldehyde and

cyclohexanone also yielded negative results for the
G. Reaction with Sodium Bisulfite for Aldehydes

Theoretically, acetone and formaldehyde were
expected to produce positive results, since they
have small groups that would possibly hinder the
attachment of the bisulfite ion to the carbonyl
carbon. On the other hand, benzaldehyde and
cyclohexanone were not expected to produce
positive results.
Upon experimentation, negative results were
recorded for both acetone and formaldehyde, which
is contrary to what was expected. This non-reaction
of acetone and formaldehyde may be attributed to
Page 10 of 12
some impurities present in the sodium bisulfite

solution which may have interfered in the reaction.
Formaldehyde:
HCHO + NaHSO3 No reaction
Acetone:
CH3COCH3 + NaHSO3 No reaction
On the contrary, both benzaldehyde and
cyclohexanone produced positive results for the
experiment, since a colloidal white precipitate was
formed in both test tubes. This reaction of the two
compounds to sodium bisulfite is due to the fact that
the bisulfite ion was able to attach itself to the
carbonyl carbon even though the carbonyl carbon
was hindered by the bulky carbon rings.
Benzaldehyde:
+
C6H6CHO + NaHSO3 C6H6CHOHSO3 + Na
Cyclohexanone
+
C6H10O + NaHSO3 C6H10OHSO3 + Na
H. Chromic Test for Aldehydes
Benzaldehyde and formaldehyde were expected
to produce positive results for experiment, since
aldehydes are easily oxidized by chromic acid to
form carboxylic acids. On the other hand,
cyclohexanone and acetone were not expected to
produce positive results.
Upon
experimentation,
acetone
and
cyclohexanone produced the expected negative
result. Since both of them are ketones, they cannot
be oxidized easily by chromic acid due to their
stability and tendency to resist reaction.
Acetone:
CH3COCH3 + 2CrO3 + 3H2SO4 No reaction
Cyclohexanone:
C6H10O + 2CrO3 + 3H2SO4 No reaction
For benzaldehyde, an unexpected negative
result was recorded, since a dark yellow color was
recorded instead of green. The negative result can
be attributed to the difficulty of the bisulfite ion in
oxidizing benzaldehyde, since the presence of the
aromatic ring makes it harder for the bisulfite ion to
attach itself to the carbonyl carbon (sterically
hindered).
C6H6CHO + 2CrO3 + 3H2SO4 No reaction

For formaldehyde, the expected positive result
was recorded due to the appearance of chromous
sulfate in the solution. Due to the easiness of
6+
oxidizing formaldehyde into formic acid, the Cr was
3+
readily reduced to Cr , which caused the formation
of the light blue green color.
HCHO + 2CrO3 + 3H2SO4 3HCOOH +3H2O +
Cr2(SO4)3
IV.
Conclusion and Recommendation
The objectives of the experiment were met after

the experiment. This is due to the fact that the
physical properties of aldehydes and ketones were
observed using the four test samples. However,
some unexpected results were recorded, such as
the non-oxidation of formaldehyde in potassium
permanganate, non-oxidation of benzaldehyde in
chromic acid, and the negative results of acetone
and formaldehyde and positive results of
benzaldehyde and cyclohexanone for sodium
bisulfite.
The deviations of the experimental results from
the theoretical one may be attributed to the
impurities present in some of the samples. These
impurities present may have hindered any reaction,
or produced a new reaction which may be the
reason why the results deviated from the expected
one.
In order to avoid the confusion in determining
whether the compound is an aldehyde or a ketone, it
is recommended to conduct additional tests that
would better establish the identity of a certain
compound such as Benedicts Test and Ceric Nitrate
Test.
Sources:
(1) Oxidation of Aldehydes and Ketones.
http://www.chemguide.co.uk/organicprops/carbonyls
/oxidation.html (accessed November 23, 2014)
(2) Potassium Permanganate. http://en.wikipedia
.org/wiki/Potassium_permanganate
(accessed
November 22, 2014)
(3) Oxidation of Aldehydes and Ketones.
http://www.wikipremed.com/03_organicmechanisms.
php?mch_code=030208_030 (accessed November
22, 2014)
Page 11 of 12
(4) Oxidation of Organic Molecules by KMnO4.

http://chemwiki.ucdavis.edu/Organic_Chemistry/Rea
Reacti/Oxidation_of_Organic_Molecules_by_KMnO
4 (accessed November 22, 2014)
/docs_file.php?v=SWRlbnRpZmljYXRpb24gb2YgY
W4gVW5rbm93biDigJMgQWxjb2hvbHMsIEFsZGVo
eWRlcywgYW5kIEtldG9uZXMKaHR0cDovL3d3dy5j
aGVtLnVtYXNzLmVkdS9+c2FtYWwvMjY5L2Fhay5
wZGYKMA== (accessed November 21, 2014).
(5) An Oxidation Reaction: Adipic Acid from

Cyclohexanone. http://academic.pgcc.edu/~rgross/
LM_204_sp11/Lab%2007%20An%20Oxidation%20
Reaction--cyclohexanone%20to%20Adipic%20Acid
.doc. (accessed November 24, 2014)
(16) Smith, J. Organic Chemistry, 3 ed., New York,

NY; 2011.
(6) 2,4-Dinitrophenylhydrazine. http://en.wikipedia.

org/wiki/2,4-Dinitrophenylhydrazine
(accessed
November 20, 2014)
(7) Addition-Elimination Reactions of Aldehydes and
Ketones. http://www.chemguide.co.uk/organicprops/
carbonyls/addelim.html (accessed November 20,
2014
(8) Schiff Test. http://en.wikipedia.org/wiki/Schiff_test
(accessed November 21, 2014)
(9) Qualitative Test for Carbonyls; Unknown
Carbonyl.
http://myweb.brooklyn.liu.edu/swatson/
Site/Laboratory_Manuals_files/Exp13.pdf. (accessed
November 21, 2014)
rd
(17) Tollens Reagent. http://en.wikipedia.org/wiki/

Tollens%27_reagent (accessed November 22,
2014)
(18) Cannizzaro Reaction. http://en.wikipedia.org/
wiki/Cannizzaro_reaction (accessed November 22,
2014)
(19) Glucose. http://en.wikipedia.org/wiki/Glucose
I hereby certify that I have given a substantial
contribution to this report and I did not copy
and/or quote from any resource material unless
being cited as reference. I am make known that
failure to accomplish the second clause would
be grounds for plagiarism and a failing grade for
my final laboratory report.
(10) Fehlings Solution. http://en.wikipedia.org/

wiki/Fehling's_solution (accessed November 21,
2014)
(11) Identification of Aldehydes and Ketones.
http://www.copharm.uobaghdad.edu.iq/uploads/activ
activ%202014/lect.2year%20tagreed/Identification%
22of%20aldehyde%20and%20keton%D9%85%D8%
B9%D8%AF%D9%84.pdf (accessed November 21,
2014)
___________________________
RAZOTE, BERNARD JOMARI B.
(12) The Triiodomethane (Iodoform) Reacted with

Aldehydes and Ketones. http://www.chemguide.
co.uk/organicprops/carbonyls/iodoform.html
(13) Simple Addition to Aldehydes and Ketones.
http://www.chemguide.co.uk/organicprops/carbonyls
/addition.html (accessed November 22, 2014).
(14) Aldehydes , Ketones and Carboxylic Acids.
http://www.laney.edu/wp/cheli-fossum/files/2012/
01/7-Aldehydes-Ketones-C.-Acids.pdf
(accessed
November 23, 2014)
(15) Identification of An Unknown Alcohols,
Aldehydes, and Ketones. https://docs.askives.com
Page 12 of 12

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LBYCH63, EA2, Group # 5

Experiment #8: Aldehydes and Ketones

Potassium permanganate is a strong oxidizing

Ketones and aldehydes are somewhat similar in