CLASSIFICATION TESTS FOR HYDROXYL AND CARBONYL CONTAINING COMPOUNDS

Hans Lorenzo Mercado, Dan Angelo Matias, Renai Matic, Celine Mindanao, Carmina Mislang
Group 6 2C Medical Technology Organic Chemistry Laboratory
ABSTRACT
Hydroxyl and Carbonyl containing samples were tested in this experiment. The samples were analyzed through tests

of alcohols in water, Lucas test, Chromic Acid test, 2,4-Dinitrophenylhydrazone (2,4-DNP) test,
Fehlings test, Tollens Silver Mirror test, and Iodoform test. Lucas test differentiates primary, secondary and tertiary
involving the solubility

alcohols. Chromic test was performed to know if the sample is oxidizable. 2,4-Dinitrophenylhydrazone test was
performed for aldehydes and ketones. Fehlings Test and Tollens Silver Mirror Test are tests for aldehydes. Iodoform
test is a test for methyl carbinol and methylcarbonyl groups. The samples are n-butyl alcohol, sec-butyl alcohol, tertbutyl alcohol, acetaldehyde, n-butylaldehyde, benzandehyde, acetone, and isopropyl alcohol.

INTRODUCTION
Hydroxyl group is used to describe the
functional group OH when it is a substituent in
an organic compound. [4] Representative organic
molecules containing a hydroxyl group are known
as alcohols. Hydroxyl groups are especially
important in biological chemistry because of their
tendency to form hydrogen bonds both as donor
and acceptor. This property is also related to their
ability to increase hydrophilicity and water
solubility [1].
There are three classifications of alcohols by
the carbon to which the hydroxyl group is
attached. Primary alcohols are those in which the
hydroxyl group is attached to the carbon with
only one carbon attached. Secondary alcohols are
compounds in which the OH- is attached to a
carbon which has two other carbons attached to
it. Tertiary alcohols are compounds in which a
hydroxyl group is attached to a carbon with three
attached carbons [3].
Carbonyl group is a family of functional groups
composed of a carbon atom double-bonded to an
oxygen atom: C=O. The group is a constituent of
carboxylic acids, esters, anhydrides, acylhalides,
amides, and quinones, and it is the characteristic
functional group of aldehydes and ketones [2].
Aldehydes are organic compound containing a
terminal carbony lgroup. This functional group,
called analdehyde group, consists of a carbon
atom bonded to a hydrogen atom with a single
covalent bond and an oxygen atom with a double
bond. Thus the chemical formula for an aldehyde
functional group is -CH=O, and the general
formula for analdehyde is R-CH=O.

Ketones features a carbonyl group(C=O)

bonded to two other carbon atoms. They differ
from aldehydes in a way that the carbonyl is
placed between two carbons rather than at the
end of a carbon skeleton [3]. They are also
distinct from other functional groups, such as
carboxylic acids, esters and amides, which have a
carbonyl group bonded to a hetero atom.
The tests used in this experiment are Lucas
test,
Chromic
Acid
test,
2,4Dinitrophenylhydrazone, Fehlings test, Tollens
Silver Mirror test and Iodoform test [4]. Lucas
test often provides classification information for
alcohols, as well as a probe for the existence of
the hydroxyl group. Substrates that easily give
rise to cationic character at the carbon bearing
the hydroxyl group undergo this test readily;
primary alcohols do not give a positive result.
[4]Chromic acid test detects the presence of a
hydroxyl substituent that is on a carbon bearing
at least one hydrogen, and therefore oxidizable.
2,4-Dinitrophenylhydrazone test can be used to
qualitatively detect the carbonyl functionality of a
ketone or aldehyde functional group. Fehlings
Test and Tollens Silver Mirror Test are used to
detect aldehydes. However, Fehling's solution can
only be used to test for aliphatic aldehydes ,
whereas Tollens' reagent can be used to test for
both aliphatic and aromatic aldehydes. Iodoform
Test is a test for methylcarbinol (secondary
alcohol with adjacentmethyl group) and methyl
carbonyl group.

EXPERIMENTAL
A. Compounds Used
The compounds used are n-butyl alcohol, secbutyl alcohol, tert-butyl alcohol, acetaldehyde, nbutylaldehyde, benzandehyde, acetone, and
isopropyl alcohol.
In this experiment, the materials needed are
Lucas reagent, chromic acid reagent, 95%
ethanol, Fehlings A and B, Tollens reagent, 5%
NaOCl solution, iodoform test reagent, 2,4dinitrophenylhydrazine, Pasteur pipette, test
tubes, beaker, and the sample compounds
ethanol, n-butyl alcohol, sec-butyl alcohol, tertbutyl alcohol, benzyl alcohol, n-butyraldehyde,
benzaldehyde, acetone, acetophenone, isopropyl
alcohol and acetaldehyde.

B. Procedure
1. Solubility of Alcohols in Water
Low molecular-weight amines and oxygencontaining compounds like alcohols, carboxylic
acids, aldehydes, and ketones are the only
soluble organic compounds in water.
In five different test tubes named as A to E,
place ten drops of ethanol, n-butyl alcohol, secbutyl alcohol, tert-butyl alcohol and benzyl
alcohol into the appropriate tube. Add 1 mL of
water to each of the test tubes and shake
thoroughly. If a cloudiness results, continue
adding 0.25 mL of water at a time, with vigorous
shaking, until a homogenous dispersion results. If
no cloudiness resulted after adding 2.0 mL of
water, the alcohol is soluble in water.

2. Lucas Test
To prepare the reagent for this test, dissolve 16
g of anhydrous zinc chloride in 10 mL of conc.
HCL. Allow the mixture to cool. After cooling, add
50 mg of the sample to 1 mL of reagent in a
small vial. Cap the vial and shake vigorously for a
few seconds. Allow the mixture to stand at room
temperature. Perform the test on n-butyl alcohol,
sec-butyl alcohol, tert-butyl alcoho, and benzyl
alcohol. Observe the rate of formation of the
cloudy suspension or the formation of two layers.

3. Chromic Acid Test

This test was performed on n-butyl alcohol,
sec-butyl
alcohol,
tert-butyl
alcohol,
nbutyraldehyde, benzaldehyde, and acetone.

Dissolve 1 drop of liquid or a small amount of

solid sample in 1 mL of acetone in a small vial.
Add 2 drops of 10% aqueous K2Cr2O7 solution and
5 drops of 6M H2SO4.

4. 2,4-Dinitrophenylhydrazone test
This test was performed on acetone,
acetaldehyde, n-butyraldehyde, benzaldehyde,
and acetophenone.
To prepare the reagent for this test, add a
solution of 3 g of 2,4-dinitrophenylhydrazine in
15 mL of conc. H2SO4 slowly, while stirring to a
mixture of 20 mL of water and 70 mL of 95%
ethanol. Stir and filter it. Place a drop of a liquid
sample into a small test tube. Add 5 drops of
95% ethanol and shake it well. Add 3 drops of
2,4-dinitrophenylhydrazine. If no yellow or
orange-red precipitate forms, allow the solution
to stand for at least 15 minutes.

5. Fehlings Test
This test was performed on acetaldehyde, nbutyraldehyde, acetone, benzaldehyde, and
acetophenone.
Fehlings reagent was prepared by mixing
equal amounts of Fehlings A and Fehlings B.
Fehlings A was prepared by dissolving 7 g of
hydrated copper (II) sulfate in 100 mL of water.
Fehlings B was prepared by mixing 35 g of
Potassium sodium tartrate and 10 g of Sodium
hydroxide in 100-ml water. 1-ml of freshly
prepared Fehlings reagent was placed into each
test tube. 3 drops of the sample to be tested
was added in to the tube. The tubes were then
placed in a beaker of boiling water and changes
within 10-15 minutes were observed.

6. Tollens Silver Mirror Test

This test was performed on acetaldehyde,
benzaldehyde, acetone, n-butyraldehyde, and
acetophenone.
The reagent was prepared by adding 2 drops
of 5% Sodium hydroxide solution to 2-ml of 5%
Silver nitrate solution and mixing thoroughly.
Next, only enough 2% Ammonium hydroxide
(concentrated ammonium hydroxide is 28%)
was added drop by drop and withstirring to
dissolve the precipitate. Adding excess ammonia
will cause discrepancies on the result of the test.
Four test tubes with 1-ml of freshly prepared
Tollens reagent were prepared. Two drops each
of the samples were then added. The mixture

was shaken and allowed to stand for 10 minutes.

If no reaction has occurred, the test tube was
placed in a beaker of warm water (35-50 oC) for
5 minutes.

7. Iodoform Test
This test was performed on acetaldehyde,
acetone, acetophenone, benzaldehyde, and
isopropyl alcohol.
2 drops of each sample was placed into its
own small vial or test tube. 20 drops of fresh
chlorine bleach (5% Sodium hypochlorite) was
slowly added while shaking to each test tube
and then, mixed. The formation of a yellow
participate was noted.

RESULTS AND DISCUSSION

Table 1. Solubility of Alcohol in Water
Alcohol

Ethanol
n-butyl
alcohol
secbutyl
alcohol
tertbutyl
alcohol
Benzyl
alcohol

Amount of
water (in
mL) needed
to produce
homogenous
dispersion
1 mL
2 mL

Solubility
in water

1.25 mL

miscible

1 mL

miscible

6.5 mL

immiscible

Table 2 shows the reaction of butanol

derivatives to Lucas Test. N-butyl alcohol, secbutyl alcohol, and benzyl alcohol yielded a clear
solution when subjected to Lucas Test whereas
tert-butyl alcohol resulted to a cloudy immiscible
suspension which eventually formed two layers.

Table 3. Chromic acid test results

Substance
n-butyl alcohol
sec-butyl
alcohol
tert-butyl
alcohol
nbutyraldehyde
benzaldehyde
acetone

miscible
miscible

Results
Light
yellow
layer to light
green layer
Yellow layer to
light
green
layer
Yellow
green
layer
Orange layer
Orange to red
layer
Light
yellow
layer to light
green layer

Table 3 shows the reaction of n- butyl alcohol,

sec-butyl
alcohol,
tert-butyl
alcohol,
nbutyraldehyde, benzaldehyde, and acetone to
Chromic Acid test. N-butyl alcohol, sec-butyl
alcohol, benzaldehyde, and n-butyraldehyde
green solution whereas tert-butyl alcohol, and
acetone resulted to a yellow solution.
Table 4. 2,4-DNP results

Table 1 shows that ethanol, n-butyl alcohol,

sec-butyl alcohol, and tert-butyl alcohol are all
miscible with water with the exception of benzyl
alcohol which exhibited insolubility.
Table 2. Lucas test results
Substan Results
Inference
ce

n-butyl
alcohol
secbutyl
alcohol
tertbutyl
alcohol
Benzyl
alcohol

no
reaction
no
reaction

miscible

Cloudy
formation

immiscible

no
reaction

miscible

miscible

Substance
acetaldehyde
nbutyraldehyde
Benzaldehyde
acetone

Results
Orange ppt.
Orange ppt.
Orange ppt.
Orange ppt.

Table 4 shows the reaction of acetaldehyde, nbutyraldehyde, benzaldehyde, and acetone to

2,4-DNP test. All the samples exhibited positive
result because they all formed an orange
precipitate. Hence, 2,4-DNP test proved that the
samples are carbonyl-containing compounds and
are either aldehydes or ketones.
Table 5. Fehlings test results
Substance
acetaldehyde

Results
Brick red ppt.
2 layer:

nbutyraldehyde
Benzaldehyde
acetone

green, brown
Brick red ppt.
3 layers:
Colorless, light
blue, royal blue
Blue solution
with orange ppt.
No change

It is shown in Table 5 that acetaldehyde, nbutyraldehyde, and benzaldehyde exhibited

positive result. Acetaldehyde, in particular turned
from blue to muddy green then formed a crude
red precipitate upon heating. These three sample
compounds which exhibited positive result to
Fehlings test are all aldehydes.
Table 6. Tollens Silver Mirror test results
Substance
acetaldehyde
nbutyraldehyde
Benzaldehyde
acetone

Results
Silver
mirror;
black ppt.
gray solution
Clear solution
Gray solution

In table 6, acetaldehyde prdouced a silver

mirror with a black ppt when subjected to Tollens
test while the other compounds did not formed
any silver mirror. The formation of the silver
mirror may be affected by the preparation of the
Tollens reagent.
Table 7. Iodoform test results
Substance
acetaldehyde
nbutyraldehyde
Benzaldehyde
Isopropyl
alcohol

Results
Brown ppt.
Redish
briwn
ppt.
Yellow ppt.
Red solution

Table 7 shows that among the sample

compounds
tested,
acetaldehyde,
acetone,
acetophenone, and isopropyl alcohol exhibited
positive

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