OBJECTIVE CHARACTERIZATION ASSESSMENT OF OXYGEN-

BEARING COMPOUNDS
Acebes, Ronniel A., Arias, Abegail, Atienza, Andrea N.*, Barlis, Philine
College of Science, University of Tomas, Manila, Philippines

Abstract:

The experiment that was conducted, included ways to differentiate and analyze the various types of
oxygen-bearing organic compounds and also be able to characterize unknown samples based on its reactions and
comparing them with the other known and similar reactions. The oxygen bearing compounds, n-propanol, 2-
propanol, t-butyl alcohol, formaldehyde, acetone, and two unknown samples all underwent distinctive analysis tests.
The various tests that were completed for the analysis were the Dichromate, Tollens, Lucas, DNPH, and the
Iodoform test, which all have its own specific identification.

Introduction:

The analysis of oxygen-bearing organic compounds is useful to evaluate if the compound

has a certain alcohol, primary, secondary, or tertiary, or if the compound contains a functional

group. It is also beneficial because it guides you into distinguishing each kind of functional

group from one another by a combination of different tests. The well-known kinds of oxygen-

bearing compounds are alcohol, phenol, ether, ketone, aldehyde, ester, and carboxylic acids. The

compounds that were examined during the experiments were alcohols, such as n-propanol, 2-

propanol, Tert-butyl alcohol, an aldehyde, formaldehyde, and ketone, acetone.

Each compound contains its own substituents, for example, the alcohol has a hydroxyl

group (-OH) attached to it which is a known characteristic of the compound. There are different

types of alcohols which are classified as primary, secondary, or tertiary.

 Figure 1: Primary Alcohol Figure 2: Secondary Alcohol Figure 3: Tertiary Alcohol

A primary alcohol is an alcohol which has the hydroxyl group connected to a primary

carbon atom, it is a molecule containing a CH 2OH group. N-propanol, is the example of a

primary alcohol that was used. It has a formula of CH3CH2CH2OH. It is a colorless liquid and

can be converted to alkyl halides. A secondary alcohol has a formula CHROH. An example of

a secondary alcohol is 2-propanol which is also known as isopropanol and its chemical formula

is C3CHOHCH3. It is a colorless, flammable chemical compound that has a strong distinct odor.

It is possible for the compound to be oxidized to acetone by using oxidizing agents such as

chromic acid. A tertiary alcohol has a formula CR2OH, where R is represented by a carbon-

containing group. The simplest tertiary alcohol is known as tert-butyl alcohol, which has a

formula of (CH3)3COH. It is a solid which is colorless and melts near room temperature. It is

also miscible with water, ethanol, and diethyl ether. It is an alcohol that is more resistant to

oxidation.
Figure 4: N-propanol Figure 5: 2-propanol Figure 6: tert-butyl alcohol

An aldehyde has a carbonyl group bonded to a carbon atom on one side and a hydrogen

atom on the other side. Its structure is CHO and it consists of a carbonyl center which is a

carbon double-bonded to oxygen. The carbon atom is also bonded to hydrogen and to an R

group. The groupwithout Ris the aldehyde group, is called the formyl group. A majority of

fragrances are aldehydes. Formaldehyde is a naturally occurring organic compound with

the formula CH2O (H-CHO). Formaldehyde is the only aldehyde that bears two hydrogen atoms

as its substituents (Solomans, Fryhle & Snyder, 2014). It is the simplest of the aldehydes (R-

CHO) and is also known by its systematic name methanal. Formaldehyde is known for its

pungent odor (Solomons, Fryle, & Synder, 2014). Aldehydes as well as ketones undergo

nucleophilic addition reactions at their carbonyl groups (figure 9).

Figure 7: Aldehyde structure Figure 8: Formaldehyde structure

Figure 9: Nucleophilic addition mechanism of Aldehydes

A ketone is an organic compound with the structure RC(=O)R'. Ketones

and aldehydes are simple compounds that contain a carbonyl group (a carbon-oxygen double

bond). They are considered "simple" because they do not have reactive groups like OH or

Cl attached directly to the carbon atom in the carbonyl group, as in carboxylic acids containing

COOH. A ketone derivative, acetone is the organic compound with the formula (CH3)2CO. It is

a colorless, volatile, flammable liquid, and is the simplest ketone. Acetone

is miscible with water and serves as an important solvent in its own right, typically for cleaning

purposes in the laboratory.

 Figure 10: General structure of Ketone Figure 11: Structure of Acetone

To distinguish between primary, secondary and tertiary alcohols, acidified potassium

dichromate (K2Cr2O7) solution is used. The primary alcohols are oxidized to aldehydes and

carboxylic acids. Secondary alcohols are oxidized to ketones, while the tertiary alcohols cannot

be oxidized by dichromate. To establish a difference between primary and secondary alcohols,

the Tollens reagent is used. Adding the Tollens reagent that will give a positive result will

produce a silver mirror. It is used to distinguish between an aldehyde and a ketone. Aldehydes

react to the Tollens reagent while the ketone does not react. The Lucas test is used to give

structural information of alcohols as well as chemical properties such as level of reactivity. For

positive results of a Lucas test the results must have a turbid solution. The DNPH test is also

called the 2,4-dinitrophenylhydrazine test. It is a chemical test used to find the function of the

carbonyl group in an aldehyde or ketone. The Iodoform test oxidizes secondary alcohols to a

methyl ketone. Positive results show for the iodoform test if there is formation of a yellow

precipitate.

The purpose of the experiment 8 is to be able to differentiate various types of oxygen-

bearing organic compounds and also to characterize an unknown sample through parallel tests.

Methodology:

During the experiment, several tests were executed, which included the Dichromate,

Tollens, Lucas, DNPH, and Iodoform test. The samples given were n-propanol, 2-propanol, tert-

butyl alcohol, formaldehyde, acetone, and the two unknown samples, a and b.
 For the first test, the Dichromate test, 10 drops of each sample were used and placed in

individual test tubes. Added to each sample was 3 drops of 10% of K2Cr2O7, 2 drops of 6M of

H2SO4, and the test tubes were shaken slightly and their results were recorded.

The next test was the Tollens test, where 10 drops of each sample were used and 20

drops of the Tollens reagent was added and after 5 minutes the results were observed and

recorded.

During the Lucas test, 5 drops of each sample were used, adding 15 drops of HCL with

ZnCl2 to the test tubes. They were shaken and the time was taken for the appearance of turbidity.

The DNPH test which consisted of using 5 drops of each sample and adding 20 drops of

the DNPH reagent. The mixture was observed and recorded after 10 minutes.

The last test that took place was the Iodoform test. This test used 5 drops of each sample

with 20 drops of 10% of KI being added to each, along with 20 drops of chlorox. The results

were observed and noted.

Results and discussion:

In the first test, the Dichromate test, the samples that gave positive results were the

samples of n-propanol, 2-propanol, formaldehyde and the unknown sample a. This test is used as

a way to distinguish between the different kinds of alcohols which is why the n-propanol and the

2-propanol reacted. The tertiary alcohols cannot be oxidized by dichromate which is the reason

why it stayed the same orange color. The formaldehyde reacted because it is always readily

oxidized. To notice positive results in the dichromate test the reaction creates a blue-green color.

The original color of the solution is orange and the color changes to a green-blue solution
because oxidation had occurred (seen in figure 12). Because the unknown sample A turned blue-

green we can assume that it is one of the 3 that also turned positive.

Figure 12: Oxidation for primary and secondary alcohols (Retrieved from:
http://www.chemguide.co.uk/organicprops/alcohols/oxidation.html)

The Tollens test includes the Tollens reagent which is the chemical reagent that is used

to determine the presence of an aldehyde, which explains why out of all the samples used during

the experiment, the only one to have a positive result was the formaldehyde. A positive test

creates a mirror-coating/solid because the diamminesilver(I) complex oxidizes the aldehyde to a

carboxylate ion and in the process, is reduced to elemental silver and aqueous ammonia which

has a characteristic of a silver mirror.

The Lucas test is used to classify alcohols of low molecular weight like secondary and

tertiary alcohols which is why during the experiment the tert-butyl alcohol gave a positive result,

which was a turbid solution. The reagent involved is ZnCl2 and HCl. The reaction is a

substitution (seen in figure 13) where the alcohol is protonated when the reagent is added and

then the chloride replaces a hydroxyl group. Tertiary alcohols react immediately with the Lucas

reagent which is seen by the turbidity of the solution when the reagent is added. Secondary

alcohols may or may not react within five minutes or so and primary alcohols do not react well

with the reagent.

 Figure 13: Substitution reaction of a tertiary alcohol (Retrieved from:

http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/ClassificationTests/alcohol.htm

l)

In the DNPH test, an orange-red precipitate is a sign of a positive result using the DNPH

reagent. The acetone, formaldehyde, and unknown sample B reacted with the DNPH reagent.

The purpose of doing the test is because it is main use is associated with aldehydes and ketones.

The unknown B sample having a positive result in this test means that the unknown sample is

either formaldehyde or acetone, to figure out the what the sample is you have to compare it to the

other reactions of the other samples in the experiment. The reaction is best described as a

condensation reaction where the mechanism is shown below in Figure 14.

 Figure 14: Mechanism between DNPH reagent and an aldehyde or ketone (Retrieved by:
https://en.wikipedia.org/wiki/2,4-Dinitrophenylhydrazine)

The last test, the Iodoform test is mainly used to find the presence of a methyl ketone by

giving a positive result with a yellow precipitate when the reaction occurs. The reaction of the

iodine and base gives the yellow precipitate. The acetone was the sample that gave a positive

result. A general equation for the reaction is seen in Figure 15. Acetone and Unknown B tested

positive with this test.

Figure 15: General equation for an Iodoform test (Retrieved from:

http://www.chemguide.co.uk/organicprops/carbonyls/iodoform.html)
 Data Table:

Samples/Test: N- 2- Tertbutyl Formaldehyd Acetone Unknown Unknown B

Propano Propanol alcohol e A

Dichromate (+) blue- (+) blue- (-) red (+) blue-green (-) red (+) blue- (-) red orange

(+) green green orange orange green

blue/green

solution

Tollens (+) (-) clear (-) clear (-) clear (+) w/ silver (-) clear (-) clear (-) clear solution

mirror solution solution solution mirror coating solution solution

coating/ solid

Lucas (+) (-) clear (-) clear (+) (-) clear (-) clear (-) clear (-) clear solution

turbid solution solution turbid/cloud solution solution solution

solution y < 1 minute

within 5

minutes

DNPH (+) (-) (-) orange (-) orange (+) w/ orange (+) w/ (-) orange (+) w/ orange

red orange orange solution solution precipitate orange solution precipitate

precipitate solution precipitate

Iodoform (+) (-) clear (+) clear (-) urine (-) red (+) pale (-) clear (+) clear

yellow yellow solution yellow solution yellow yellow yellow

precipitate solution w/ yellow solution solution solution solution

precipitate w/ yellow w/ yellow

precipitate precipitate

Conclusion:

At the end of the experiment, the identities of the unknown samples can be made known

by comparing the results of each reaction with the results of the other samples. The unknown

sample As results were determined to have the most similarities with n-propanol which is what it

is concluded to be. The other unknown sample, sample B was concluded to be acetone. Each

sample used in the lab also had different oxygen-bearing compounds such as alcohols, aldehydes,

and ketones. They all have different physical and chemical properties and also have different

levels of reactivity.
 Bibliography

Books:

Bayquen, A., Cruz, C., De Quia, R., Lampa, F., Pena, G., Sarlie, A., & Torres, P. (2009).

Laboratory manual in organic chemistry. Quezon city: C and E Publishing Inc.

Solomans, Fryhle & Snyder. (2014). Organic Chemistry text book.

Websites:

Analysis of Oxygen-Bearing Organic Compounds. (n.d.). Retrieved from

https://lawaspect.com/analysis-oxygen-bearing-organic-compounds/

Tests for Alcohol. (n.d.). Retrieved from

http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendix/Classificati

onTests/alcohol.html#Lucas