Analysis of Oxygen-Bearing Organic Compounds

Fernandez, Gino Miguel*, Damiles, Johmar, De Vera, Alyssa Gail, Elio, Charlene
Lorraine

2BIOLOGY6, Department of Biology, College of Science, UST, Manila

fginomiguel@yahoo.com

Abstract
This experiment deals with the discriminating the different types of oxygen-bearing organic compounds through a
series of tests, these tests are namely Dichromate Test, Tollens Test, DNPH Test, Iodoform Test, and Lucas Test. The
samples used for these tests were methanol, isopropanol, tert-butanol, formaldehyde, acetone, and an unknown
sample assigned to the researchers. It was through the use of the different reagents and techniques that the
characteristics of each standard compounds were observed and distinguished. After the reactions have been noted, it
was compared to the reactions with that of the unknown.
Keywords: Oxygen-bearing, Dichromate, Tollens, DNPH, Iodoform, Lucas Tests

Introduction
The analysis of oxygen-bearing organic
compounds was used to identify whether the
mixture contained an alcohol, whether primary,
secondary, or tertiary, or a functional group. This
experiment focused on distinguishing the
several kinds of functional groups from each
other. Standard compounds were used to
identify the characteristics of each group
present. The following reagents were used as
standards:
Primary alcohol: methanol. Primary alcohol has
a characteristic where carbon atom with a
hydroxyl group has at least 2 hydrogens and any
organic group attached on it. The carbon atom
and R form an alkyl group.
Secondary alcohol: isopropanol. A secondary
alcohol has a characteristic of only one
hydrogen attached on a carbon with a hydroxyl
group. This carbon is then attached to 2 alkyl
groups.
Tertiary alcohol: t-butanol. Tertiary alcohol has a
characteristic of no hydrogens attached on a
carbon with a hydroxyl group. The carbon is then
connected to three alkyl groups.
Aldehyde: Formaldehyde. This functional group
has a carbonyl group attached to an alkyl or

aromatic group. This can be reduced to primary

alcohol.
Ketone: Acetone. This functional group has a
carbonyl group attached on two alkyl or aromatic
groups.
Besides these given reagents, an unknown
reagent was given to the researchers and the
results of the tests were used as a basis to find
the given unknown. The following chemical tests
were used:
Dichromate Test: Dichromate oxidizes primary or
secondary alcohols and aldehydes to ketones or
carboxylic acids.
Tollens: Tollens reagent oxidizes aldehydes to
ammonium salts of carboxylic acids.
Lucas: Alcohols are converted to alkyl chlorides
with Zinc Chloride. Different alcohol types
responds at different rates.
DNPH: DNPH reagent condenses with carbonyl
containing molecules.
Iodoform: NaOCl oxidizes a methylocarbonyl
group and in the process yield a yellow
precipitate of Iodoform.

Methodology
Dichromate Test
For the Dichromate Test, all the reagents
were used for testing. The researchers mixed 8
drops of the sample and standards in separate
test tubes with 2 drops 10% K2Cr2O7 and 5 drops
6M H2SO4. The positive visible result for this test
is a green or blue-green solution. The results
were then observed and recorded.
Tollens Test
For the Tollens Test, only the tertiary
alcohol and the aldehyde were used for testing.
The researchers mixed 2 ml of freshly made
Tollens reagent and 5 drops of the sample in
separate test tubes. This solution was then left
to stand for 5 minutes. This process should
create a silver precipitate, however, if no
precipitate forms, the mixture should be placed
in a 70oC water bath for 5 minutes. The positive
visible result for this test is a silver mirror coat.
The results were then observed and recorded.
Lucas Test
For the Lucas Test, only the alcohols, the
primary, secondary, and tertiary alcohols, were
used for testing. The researchers mixed 5 drops
of the sample, 15 drops of HCL and a very small

Tests
Dichromate
Lucas

Methanol
Blue-green
liquid (+)
Colorless
liquid (-)

isopropanol
Blue-green
liquid (+)
Colorless
liquid (-)

Iodoform

DNPH Test
For the DNPH Test, only the functional
groups, aldehyde and ketone, were used for
testing. The researchers mixed 5 drops of the
sample and 1 ml DNPH reagent in separate test
tubes. It was left to stand for 15 minutes. A
precipitate should form for this test, however, if
no precipitate forms, the test tube should be
subjected to a 15 minute water bath at 70 oC.
The positive visible result for this test should be
a red, orange, or yellow precipitate. The results
were then observed and recorded.
Iodoform Test
For this test, only the secondary alcohol
and the ketone were used for testing. The
researchers mixed 5 drops of the sample and 20
drops of NaOCl solution in separate test tubes. A
precipitate should form for this test, however, if
no precipitate forms, the solution should be
placed in a 70oC water bath for 5 minutes. The
positive visible result for this test should be a
yellow precipitate. The results were then
observed and recorded.

t-butanol
Orange
liquid (-)
Turbid liquid
(+)

DNPH
Tollens

amount of ZnCl2 solid in separate test tubes. The

tubes containing the mixture were then
discomposed until turbidity has occurred. The
positive visible result for this test is an
occurrence of turbidity in the mixture.

Formaldehyd
e
Blue-green
liquid (+)
Yellow ppt (+)

Brownish
liquid (-)

Acetone
Orange
liquid (-)
Orange ppt
(+)

Silver
liquid
with gray solid
(+)

Yellow-white
ppt
with
colorless
liquid (+)
Table 1.1: This table shows the results for the different tests performed

Yellow
(+)

ppt

Unknown
Orange
liquid (-)
Colorless
liquid (-)
Orange
liquid (-)
Brownish
liquid (-)
Yellow ppt
with
colorless
liquid (+)

Results and Discussion

By subjecting the samples to the given
tests, the researchers were able to determine
whether the reagents are alcohols, be it primary,
secondary or tertiary, or functional groups, be it
an aldehyde or a ketone.
According to the results of the dichromate
tests, the samples methanol, isopropanol, and
formaldehyde gained a positive visible result,
which is blue-green or green solution, which
means that methanol and isopropanol are
primary and secondary alcohols respectively,
and formaldehyde is indeed, an aldehyde. On
the other hand, t-butanol and acetone garnered
a negative result, therefore proving that t-butanol
is a tertiary alcohol and acetone is a ketone.
Lucas Test, which is used to determine
whether a compound is a primary or a
secondary alcohol. The sample t-butanol gained
a positive result, therefore, making it tertiary
alcohol. Methanol and isopropanol gained a
negative result, therefore, they may either be a
primary or secondary alcohols.
DNPH Test, which determines whether a
compound contains a functional group. The
samples formaldehyde and acetone were the
only solutions tested and they both gained a
positive result, therefore, formaldehyde and
acetone does, indeed, contain a functional
group, be it an aldehyde or a ketone or a
carboxylic group.
Tollens Test, which determines whether the
compound contains aldehydes. Only the
samples formaldehyde and t-butanol were
tested. Formaldehyde gained a positive result
while t-butanol gained a negative result.
Therefore, formaldehyde contains the functional
group aldehyde and t-butanol does not.
Iodoform Test, which is used to indicate
particular alcohols, particularly tertiary alcohols
and ketones. Only the compounds isopropanol
and acetone were subject to this test. Both
compounds garnered a positive result, and
therefore these 2 compounds may either be an
alcohol or a ketone group.
For the unknown sample, all tests were
performed. The unknown sample yielded a

negative result on the Dichromate, Lucas,

DNPH, and Tollens Test, the unknown sample
only gained a positive visible result from the
Iodoform test. The Iodoform test is used whether
the compound is a tertiary alcohol or a ketone
group. We can deduce that the unknown sample
is either a tertiary alcohol or a ketone group.
According to the results of the Lucas test, which
determines whether a compound is a
primary/secondary alcohol if positive or a tertiary
alcohol if negative, the result came out negative,
therefore the unknown is a tertiary alcohol. So
we can conclude that the researchers unknown
sample is a tertiary alcohol or more specifically,
t-butanol.

Conclusion
The various tests performed in this
experiment were used to identify or classify on
which functional groups the samples used in the
experiment belong to. These were caused by
certain atoms reacting to one another, showing
the positive or negative result of the respective
tests. Using the results from the control tests,
the researchers were able to determine the
unknown compound that was assigned to them.
Using these tests, one may be able to determine
and classify to where a specific functional group
a compound belong to.

Acknowledgements
To K.B, P.R., J.V. and T.C., for helping the
researcher with his inquiries.
To the rest of the researchers circle of friends,
for the moral support they have provided.
To Sir Tan and Sir Bias, for helping out the
researchers with all the problems they had and
answering the questions they have asked.

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