EXPERIMENT 9

TITLE: ALDEHYDE AND KETONES: CHARACTERIZATION OF AN UNKNOWN

OBJECTIVE:
To distinguish unknown solution based on the characteristic of aldehyde and ketones.
INTRODUCTION:

Aldehydes
and ketones
share the carbonyl functional group which features
carbon doubly bonded to oxygen. Ketones have two carbon atoms bonded to the carbonyl
carbon and no hydrogens. Aldehydes have at least one hydrogen bonded to the carbonyl
carbon; the other attachment may be to a carbon or hydrogen. In all cases the carbon(s) that
are attached to the carbonyl group may be aliphatic (not part of an aromatic ring) or aromatic
(part of an aromatic ring). Since they share the carbonyl group, aldehydes and ketones share
much of their chemistry, but they are different enough to be considered different classes of
compounds. This situation is similar to that of alcohols and phenols which both share the -OH
group.
The different between aldehyde and ketone is by having a hydrogen atom attached to the
carbonyl group. This makes the aldehydes very easy to oxidize. Ketones don't have that
hydrogen atom and are resistant to oxidation. They are only oxidized by powerful oxidizing
agents which have the ability to break carbon-carbon bonds.

Cyclohexanone is the organic compound with the formula (CH 2)5CO. This colorless
oil has an odor reminiscent of peardrop sweets as well as acetone. Over time,
samples assume a yellow color due to oxidation. Cyclohexanone is slightly soluble
in water (5-10 g/100 mL), but miscible with common organic solvents.
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring
with a formyl substituent. It is the simplest aromatic aldehyde and one of the most
industrially useful. This colorless liquid has a characteristic pleasant almond-like
odor. In fact, benzaldehyde is the primary component of bitter almond oil and can
be extracted from a number of other natural sources.
Acetophenone is the organic compound with the formula C 6H5C(O)CH3. It
is the simplest aromatic ketone. This colorless, viscous liquid is a
precursor to useful resins and fragrances.

PROCEDURE:
1. 2,4-dinitrophenylhydrazine (DNP)
i.
Each solution was put into different test tubes.
ii.
1ml of DNP was added into each test tube.
iii.
The test tubes were shakes vigorously.
iv.
The color changes were observed.
2. Chromic acid test reagent (Jones Reagent)
i.
1ml reagent grade acetone was put into 5 difference test tubes.
ii.
1 drop of each solution was put into the test tube.
iii.
Several drops of chromic acid were added while shaking.
3. Tollens reagent test
i.
All five test tubes were washed with hot nitric acid and were rinsed with
distilled water.
ii.
Each solution was put into different test tube
iii.
Chromic reagent was added dropwise into each test tube.
iv.
If there are no reaction occurs, the test tube was warmed gently in water
bath.
v.
After the test, the contents of the test tube were poured into the sink and the
test tube was washed with dilute nitric acid.
4. Iodoform test.
i.
Water bath between 60-70C was used.
ii.
6 drops of unknown and 3 others solutions were added in 2ml 1,2
dimethoxyethane in different test tube.
iii.
10% NaOH was added into each of the test tube.
iv.
All the test tubes were places in water bath. It was heat in water bath for 5
minutes.
v.
The dark color should be discharged, If not, more 10% NaOH was added.
5. Ferric chloride test
i.
Each of the solutions was put into 5 different test tubes.
ii.
The ferric chloride solution was added into each of the test tubes drop wised.
iii.
Any changes of the solution were observed.

RESULT:
Cyclohexanone

Benzaldehyde

Acetophenone

2,4dinitrophenylhydrazine

Light yellow
precipitate

Orange
solution

Oily yellow
solution

Oily light
yellow

Light
orange
precipitate

Chromic acid test

reagent (Jones
Reagent)
Tollens reagent

Dark brown
precipitate, oily

Dark
orange/red

Reddishbrown, oily

Dark brown

Dark green

Cloudy solution

Oily layer
form

Oily layer form

Cloudy
solution

Clear solution

2 layers
[cloudy
(upper), grey
(bottom)]
Red brown,
oily

2 layers[ milky
(upper), clear
solution
(bottom)]
Dark brown

2 layers of
yellow
solution
Peach
solution with
precipitate

2 layers [light
yellow
(upper)]

2 layers,
[cloudy(upper),
light yellow
(bottom)], oily

-After heat

Iodoform test reagent

Dark red, oily

Ferric chloride test

reagent

2 layers, oily

Unknown X

Dark
yellowish
brown, oily
2 layers,
yellow
solution

Unknown Y

2 layers
[oily(upper)
, grey
(bottom)]
2 layers,
dark red
Light
orange

DISCUSSION:
Generally the chromic acid test reagent (Jones reagent) and Tollens reagent was to identify
aldehyde. Iodoform test reagent is to identify methyl ketone, Ferric chloride test reagent is to
identify whether the compound is enol content.
2,4-dinitrophenylhydrazine can react with both aldehyde and ketone. By adding 2,4dinitrophenylhydrazine, literally, an aldehyde compound will change to orange, yellow or red
precipitate. From our result, benzaldehyde and unknown Y satisfy the theory. As for
cyclohexanone, acetophenone and unknown X disobey the theory. From the result also those
that disobey theory are oily solution. These show the characteristics of ketone, the reason why
the ketone give oils because it was not solidify. From the color shows provide information about
compound that are unconjugate (yellow) and conjugate (orange to red).

Reaction of benzaldehyde

Reaction of cyclohexanone

Reaction of Acetophenone
Chromic acid test reagent (Jones reagent) also called oxidation test. Theoretically, a positive
test for aldehyde consists in the production of an apaque suspension with a green to blue color.
Aldehyde work with chromic acid test reagent because of it was ready oxidation of aldehydes.
From the result, it seems that the unknown Y gave dark green, this could be aldehydes. At the
other hands, all ketone form red to brownish solution. The benzaldehyde not turning into green
maybe because it took time to react with chromic acid.

The possible chemical equation for unknown Y

For Tollens reagent test, the positive test should have the formation of silver mirror or black
precipitate. However, our result doesnt indicate any of silver mirror, except for unknown Y which
have little grey solution in the middle, these maybe because we done mistakes where we
doesnt adding 10% of NH3 solution and 10% of NaOH solution. Either unknown X or Y, the
chemical equation that may involve in the reaction is as below.

In Iodoform test, the iodoform itself is a yellow precipitate (mp 119-121oC). Literally, pale yellow
precipitate indicates the presence of methyl ketone, but the other ketone will discharge color
and will not form iodoform precipitate. Refers to the result we have, the ketone that are
cyclohexanone and benzophenone doesnt not show any trace of yellow precipitate. This may
related to the other ketone rather than methy ketone. However, unknown x show a little yellow
but no precipitate form, it show little characteristic of ketone although it is not a methyl ketone.

The chemical equation if the compound is methyl ketone

Ferric chloride test reagent was used to detect any presence of a compound with high enol
content. The color is the result of enolate complexion with Fe(III) ion. Literally, the positive result
gave red, blue, purple or green color. From our result, all five solution doesnt shows any of the
possible color, mean that there may not contain enol.

CONCLUSION:
The experiment involves very sharp observational skill, where we should observe any changes
of color and forming or layers or precipitate, this is because the product will determine the
reliability of unknown solution. We were expecting the unknown solution will have any parallel
similarities to the other three compounds, which are cyclohexanone, benzaldehyde and
acetophenone. These three compounds do help in comparing the changes in order to identify
the unknown x and Y. To obtain the right identification, we compared the observation we took
during experiment to the literature sources. From that we conclude that the unknown X is ketone
and unknown Y is an aldehyde.

References:
Aldehydes and Ketones. Retrieve on February 6, 2010 from
http://usm.maine.edu/~newton/Chy251_253/Lectures
Online Lab Manual Home: Tests for Aldehydes and ketone. Retrieved on February 6, 2010 from
http://www.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual
Peter Keusch. Addition of 2,4-dinitophenylhydrazine to aldehyde and ketones. Retrieved on
February 6, 2010 from http://video.uniregensburg.de:8080/ramgen/Fakultaeten/Chemie/Org_Chemie
Peter Keusch. Tollens reaction Silver Mirror Test. Retrieved on February 6, 2010 from
http://video.uni-regensburg.de:8080/ramgen/Fakultaeten/Chemie/Org_Chemie/

QUESTION:
1. Using chemical tests, how would you distinguish among 2-pentanone, 3-pentanone and
pentanal?
Sodium bisulphate test: 2-pentanone being a methyl ketone when treated with saturated
solution of sodium bisulfite gives a white precipitate of 2-pentanone sodium bisulphate
addition compound whereas 3-pentanone does not.
CH3CH2CH2COCH3 + NaHSO3 CH3CH2CH2-C(OH)(SO3Na)-CH3
(2-pentanone sodium bisulfite addition compound) OH and SO3Na are present on the
same carbon.
CH3CH2COCH2CH3 + NaHSO3 no reaction
Only pentanal will give a positive Tollens test and only 2-pentanone will give a positive
iodoform test. Tollens reagent (silver mirror test) is used as a test for aldehydes, which
are oxidized to carboxylic acids. The iodoform test is a qualitative chemical test for the
detection of ketones and aldehydes carrying an alpha methyl group. 3-Pentanone will
negative results in both of these tests.
2. Draw the structure of two geometric isomers, C5H8O, that give a positive iodoform test.
Cis- isomer

Trans- isomer