Name: Judith Eliza A. Mariano Instructor: Engr.

Aldrin Lorrenz Chan

Section: 2- ChE B Date Experiment Performed: March 28, 2017
Group: 7 Date Experiment Submitted: March 28, 2017

Experiment 8: Analysis of Oxygen-Bearing Organic Compounds

INTRODUCTION
An Alcohol is an organic compound in which a hydroxyl group is attached (-OH) to a
carbon atom. Alcohols could be classified as primary, secondary, or tertiary alcohol.
A primary alcohol is an alcohol whose hydroxyl group is attached to a primary carbon, a
carbon that has only one carbon attached to it (Solomons, Fryhle & Snyder, 2014). In this
experiment, methanol (CH3OH), also known as methyl alcohol, is a primary alcohol to be used in
this experiment.
A secondary alchohol is an alcohol whose hydroxyl group is attached to a secondary
carbon, a carbon that bears the two other carbons (Solomons, Fryhle & Snyder, 2014). 2-
propanol(CH3CH(OH)CH3), also known as isopropyl, is a secondary alcohol to be used in this
experiment.
A tertiary alchohol is an alcohol whose hydroxyl group is attached to a tertiary carbon, a
carbon that bears three other carbon atoms (Solomons, Fryhle & Snyder, 2014). A tertiary
alcohol of particular interest in this experiment is 2-methyl-2-propanol, also known as tert-butyl
alcohol ((CH3)3COH).
Moreover, aldehyde is a functional group that contains a carbonyl group (C=0).The
carbonyl group of an aldehyde is bonded to one hydrogen and one carbon atom. One exemption,
and is of particular interest, is the formaldehyde(CH2OH), commonly known as formalin, which
is the only aldehyde bearing two hydrogen atoms (Solomons, Fryhle & Snyder, 2014).
Another organic compound are the ketones; like aldehydes, ketones also contain a
carbonyl group. However, the carbonyl groups in ketones is bonded to two carbon atoms
(Solomons, Fryhle & Snyder, 2014). Acetone ((CH3)2CO) is a ketone to be used in this
experiment.
This experiment aims to differentiate the various types of oxygen bearing organic
compound and to characterize an unknown sample through performing different chemical tests.
In order to identify the unknown sample, five reference standard organic compounds (tree
alcohols, a ketone, and an aldehyde) and five classification tests were used (Dichromate Test,
Tollen’s Test, Lucas Test, DNPH Test, and Iodoform Test).
Dichromate test, also known as Jones Oxidation test, is mainly used to distinguish
between primary, secondary, and a tertiary alcohol based on their oxidation reactions. It is a
functional-class test for alcohols and aldehydes. Positive visible result is the presence of intense
blue green solution (Pavia, Lampman, Kriz, & Engel, A microscale approach to organic
laboratory techniques, 2013).
The second test is Tollen’s Test. It is also called “Silver-Mirror Test”. It is used to
distinguish between an aldehyde and a ketone, a functional class test for aldehydes based on their
oxidation reactions. Positive visible result is the formation of silver mirror coating in the test tube
(Pavia, Lampman, Kriz, & Engel, A microscale approach to organic laboratory techniques,
2013).
Thirdly, the Lucas Test is used to classify alcohols in accordance with their reactivity. It
is both a functional class test and chemical test that provides structural information of alcohols.
Positive visible result yields a turbid solution (Pavia, Lampman, Kriz, & Engel, A microscale
approach to organic laboratory techniques, 2013).
The fourth test is DNPH test. This test is further called 2-4-dinitrophenylhydraline test.
This chemical test is used to detect the carboyyl group functionality in aldehydes and ketones
basing from condensation reaction; therefore, it’s a functional-class test for aldehydes and
ketones. Positive visible result yields to formation of red-orange precipitate (Pavia, Lampman,
Kriz, & Engel, A microscale approach to organic laboratory techniques, 2013).
Lastly, the Iodoform test is mainly used to identify methyl ketones. This test provides
structural information not only for ketones, but also for alcohols basing from the oxidation
reactions. Positive visible result yields a yellow precipitate (Pavia, Lampman, Kriz, & Engel, A
microscale approach to organic laboratory techniques, 2013).

METHODOLOGY
In this experiment, parallel chemical testing was followed all throughout the experiment.
Five chemical test were conducted- Dichromate Test, Tollen’s Test, Lucas Test, DNPH Test, and
Iodoform Test.
For the Dichromate Test, the reference standard and samples used were methanol,
isopropyl, t-butanol, acetone, formalin, and the unknown sample. Eight drops of the sample and
standards were mixed in separate test tubes with two drops of K2Cr2O7 and five drops of 6M
H2SO4. The results were observed and recorded.
For the Tollen’s Test, 2mL of Tollen’s reagent and five drops of the sample were mixed.
The chemical reactions were timed 5 minutes. In an event where a silver precipitate is not
formed, the solution was placed in a 70ºC water bath for 5 minutes. The results were observed
and recorded. The samples and standards used were formalin, isopropyl, methnol, and the
unknown sample.
For the Lucas Test, the reference standard sample used were methanol, isopropyl, and the
unknown sample. Five drops sample, fifteen drops of concentrated HCl and a corn grain amount
of ZnCl2 solid were mixed. The test tube was shook and the appearance of turbidity was timed.
 For the DNPH Test, the reference standard sample used were acetone, t-butanol, and the
unknown sample. Five drops of the sample, 1mL ethanol, and 1mL DNPH reagent were mixed.
The chemical reactions were timed 15 minutes. When no precipitate was formed, the solution
was placed in a 70ºC water bath for 5 minutes. The results were observed and recorded.
Lastly, for the iodoform test, the reference standard and samples used were methanol,
isopropyl, t-butanol, acetone, formalin, and the unknown sample. Five drops of sample, twenty
drops of commercial Chlorox (NaOCl solution) were mixed. When no precipitate was formed,
the solution was placed in a 70ºC water bath for 5 minutes. The results were observed and
recorded.
DATA SHEET
Table 1. Data of Results of the Chemical Tests for Reference Standards and Unknown Sample
Chemical Tests Unknown Sample Reference Positive Visible
Standards Result
+ -
Dichromate Test - Formalin Acetone Green solution
Isopropyl t-butanol
Methanol
Tollen’s Test - Formalin Isopropyl Mirror coat
Methanol
Lucas Test - Isopropyl Turbid fast
DNPH Test - Acetone t-butanol Red orange
precipitate
Iodoform Test + Formalin Yellow precipitate
Isopropyl
Methanol
Acetone
t-butanol

RESULTS AND DISCUSSION

Table 1 shows the results of the following chemical tests to the standard solution and
unknown sample. For the Dichromate Test, formalyn, isopropyl, and methanol reacted with a
blue green solution. For the Tollen’s Test, only formalin reacted with a mirror coat. While for the
Lucas test, isopropyl gave a turbid solution.
Since Dichromate Test is used to distinguish primary, secondary alcohols and aldehydes,
formaline, isopropyl, and methanol resulted positive. Formalin, isopropyl, and methanol are
therefore oxidizables and had to undergo Tollen’s Test. Tollen’s Test is used to distinguish an
aldehyde and a ketone. For this test formalin resulted positive and is therefore and aldehyde.
Isopropyl and methanol resulted negative in the Tollen’s test. To classify the alcohols, both
underwent Lucas Test. Isopropyl resulted positive and is therefore a secondary alcohol, while
methanol is a primary alcohol.
 Acetone and t-butanol resulted negative in the dichromate test. Therefore both of them
are non oxidizable and both had to undergo DNPH test. The reaction of acetone with the test
gave a red-orange precipitate and the t-butanol did not. Therefore, acetone is a ketone and t-
butanol is a tertiary alcohol.
As for the iodoform test, only the unknown sample resulted positive. Iodoform test is a
test used to identify methyl ketones. Knowing this, acetone and isopropyl should have resulted
positive in this test.
The unknown sample resulted negative in the Dichromate and DNPH test, therefore the
unknown sample is a tertiary alcohol. The unknown sample however resulted positive in the
Iodoform test, which means that it is a ketone.
CONCLUSIONS AND RECOMMENDATIONS

REFERENCES
Solomons, T.W., Fryhle, C.B., Snyder, S.A., (2014). Organic Chemistry (11th ed). Danvers,
MA: John Wiley and Sons, Inc.
Pavia, D. L., Lampman, G. M., Kriz, G. S., & Engel, R. G. (2013). A microscale approach to
organic laboratory techniques (5th ed.). Belmont, CA: BrooksCole, Cengage Learning.
Organic Qualitative Analysis Retrieved April 17, 2017. Retrieved from Foothill:
www.foothill.edu/psme/armstrong/pdfdocuments/qualanal