EXPERIMENT 8: PROPERTIES OF ORGANIC COMPOUNDS WITH CARBONYL GROUP

I. Objectives: To compare chemical reactivity of organic compounds with carbonyl

group.

II. Apparatus: test tubes, 10 ml graduated cylinder, Bunsen burner, water bath, wire
gauze, beaker(250 ml), test tube holder, test tube rack

III. Materials: Tollen’s reagent, formalin, benzaldehyde, formaldehyde, acetone,

Fehling’s A, Fehling’s B, Schiffs reagent, 0.5% resorcinol, conc. sulfuric acid, diluted
sulfuric acid, ethanol, 10%sodium hydroxide, I2 in KI , potassium dichromate. formic
acid, acetic acid, benzoic acid, litmus paper, , acid, 3 g. soda lime, ethyl acetate,
methyl salicylate, amyl acetate, methyl benzoate

IV. Procedure and Observation

A. The properties of different organic compounds namely, Formaldehyde, Benzaldehyde,
Acetone, Formic Acid, Acetic Acid, and Benzoic Acid. They were classified according to
their color, odor, flammability, volatility, solubility in water, and solubility in alcohol.
B. For the second part of this experiment, Tollen Test was conducted. Three to five drops
of Formalin, Benzaldehyde, Acetone, Acetic Acid, Benzoic Acid solution, and Formic
Acid was placed in six separate test tubes. Three to five drops of Tollen’s Reagent was
added on each test tube. Afterwards, the contents were mixed and were warmed gently
in a water bath.
C. For the third part of this experiment, Fehling’s Test was conducted. Three to five drops
of Formalin, Benzaldehyde, Acetone, Acetic Acid, Benzoic Acid solution, and Formic
Acid was placed in six separate test tubes. Three ml of Fehlings A and another Three ml
of Fehlings B solution were mixed in a separate test tube. One ml of Fehling’s solution
was added on the six separate test tubes.
D. For the fourth part of this experiment, Resorcinol Test was conducted. Three to five
drops of Formalin, Benzaldehyde, Acetone, Acetic Acid, Benzoic Acid solution, and
Formic Acid was placed in six separate test tubes. Two drops of 0.5% resorcinol solution
was added on each test tube and was shaken. The test tubes were inclined and were
carefully added with 1.0 ml of concentrated sulfuric acid. This is to prevent from the two
liquids from mixing together.
E. For the fifth part of this experiment, the oxidation of the given organic compounds were
observed. A pinch of potassium dichromate, 0.5 ml of concentrated sulfuric acid and 0.5
ml of formaldehyde and 1 ml of water were mixed together in a test tube. The solution
was heated gently and a piece of blue litmus paper was held near the vapor evolved.
The procedures were repeated using benzaldehyde instead of formaldehyde, followed
by acetone, formic acid, acetic acid and benzoic acid.
F. Lastly, Iodoform test was conducted. In one ml of acetone, 1.5 ml of 10% NaOH solution
and 0.5 ml of water were added. Drop by drop of Iodine in KI were added until prominent
yellow color is obtained. The solution was then warmed gently. The procedure was
 repeated using using benzaldehye, formaldehyde, formic acid, acetic acid & benzoic
acid.

V. Illustrations

FORMALDEHYDE
BENZALDEHYDE

ACETONE

TOLLEN’S TEST

FEHLING’S TEST
FORMALDEHYDE ACETIC ACID

BENZALDEHYDE
ACETONE
 RESORCINOL TEST

ACETONE

BENZALDEHYDE FORMALDEHYDE

OXIDATION

BENZALDEHYDE

ACETONE FORMALDEHYDE
 VI. Results with Theory

The physical properties of organic compounds with carbonyl groups were observed and
results were noted as shown in Table 1.

Formic Acetic Benzoic

Properties Formaldehyde Benzaldehyde Acetone
Acid Acid Acid
Color Colorless Pale Yellow Colorless Colorless Colorless Colorless
Vinegar
Almond like Unpleasan
Odor Unpleasant Unpleasant like sour odorless
pleasant t
odor
Flammabilit Non- Non- Non-
Flammable Flammable Flammable
y flammable flammable flammable
Non- Non-
Volatility Volatile Volatile Volatile Volatile
volatile Volatile
Solubility in Slightly Slightly
Miscible Miscible Miscible Miscible
Water miscible Miscible
Solubility in
Miscible Miscible Miscible Miscible Miscible Miscible
Alcohol
Table 1. Summary of Results for the properties of organic compounds with carbonyl groups

Formaldehyde is a clear and colorless liquid with a strong and unpleasant odor. Pure
formaldehyde is not handled commercially handled commercially because it tends to polymerize
exothermally and may ignite. It is also identified as a Volatile Organic Compound (VOC)
because of its frequent occurrence in indoor air and the serious health outcomes resulting from
exposure. It is soluble in water because the intermolecular interaction it exhibits is dipole-dipole
interactions. The oxygen is more electronegative than the carbon, so the oxygen holds the
partial negative charge. The hydrogens are not directly bonded to oxygen, so this molecule
does not exhibit hydrogen-bonding with itself. In the same manner, it is also soluble in alcohol. It
is the simplest aldehydes which makes it soluble in both alcohol and ethers.

Benzaldehyde is a liquid that has a pale yellow color in nature with a bitter-almond-like odor.
It is a combustible liquid and is volatile because of its fungicidal property. It is slightly soluble in
water because the lone pair on oxygen atom of benzaldehyde is completely involved in
conjugation making it less available to form hydrogen bonding with water. On the other hand, it
is completely soluble in ethanol and diethyl ether.

Acetone is a colorless liquid with an unpleasant pungent odor. Acetone has the weakest
intermolecular forces, so it evaporated most quickly making it a volatile substance. Acetone has
a flashpoint of 0°F (-18°C) makes it a highly flammable liquid, which can ignite even as a low
concentration mixture with water. Acetone is soluble in water because the slightly positive
charge on each hydrogen can attract slightly negative oxygen atoms on other water molecules,
forming hydrogen bonds. If acetone is added to water, acetone would completely dissolve.
Acetone is a good solvent due to its ability to dissolve both polar and non-polar substances.

Formic Acid is a colorless and fuming liquid with an unpleasant pungent odor. Formic acid is
not flammable but a combustible liquid. Formic acid is about ten times stronger than acetic acid.
It is used as a volatile pH modifier in HPLC and capillary electrophoresis. Formic acid is miscible
with water and most polar organic solvents, and somewhat soluble in hydrocarbons. Industrially,
formic acid is produced from methanol.

Acetic Acid is a clear and colorless liquid with vinegar-like sour odor. Acetic acid, just like
formic acid, is not flammable but instead a combustible liquid. Acetic acid is considered a
volatile organic compound. Acetic acid is soluble in both alcohol and water because acetic acid
is able to form many new hydrogen bonds to water molecules and so this results in a highly
favourable interaction, leading to the high solubility of acetic acid in water.

Benzoic acid is a colorless and crystalline solid that is odorless. Benzoic may burn but it
does not ignite. Benzoic acid is considered as steam volatile. Benzoic acid is poorly soluble in
water because of a polar carboxylic group, the bulk amount of the benzoic acid molecule is non-
polar. It is only the carboxylic group that is polar. On the other hand, benzoic acid is very soluble
in alcohol.

On the next part of the experiments, various test procedures were performed to determine
different reactions as shown in table 2.

Reagent / Formic Acetic Benzoic

Formaldehyde Benzaldehyde Acetone
Tests Acid Acid Acid
No No No No
Tollen’s Silver mirror Silver mirror
reaction reaction reaction reaction
Brick red No No No No
Fehling’s No reaction
precipitate reaction reaction reaction reaction
Red
precipitate at No No No No
Resorcinol No reaction
the junction reaction reaction reaction reaction
of two liquids
From orange From orange No
Oxidation Green Green Green
to green to green reaction
No No No
Iodoform No reaction No reaction Yellow
reaction reaction reaction

In performing Tollen’s Test, only formaldehyde and benzaldehyde produced any reactions. It
can be observed that when both formaldehyde and benzaldehyde were heated in a water bath,
the test tube was filled with scattered black pigments. Tollen’s reagent is a mild oxidizing agent
that is composed of silver ions in an aqueous basic solution of ammonia. When aldehyde is
added to tollen's reagent, Ag2O is reduced to silver which deposits as black precipitate or silver
mirror. Meanwhile, ketones are not oxidized therefore, no silver mirrors were formed.

In performing Fehling’s Test, only formaldehyde produced a brick red precipitate.

Formaldehyde has alpha hydrogen. Thus, it will show positive Fehling's test. The reaction
requires heating of aldehyde with Fehling's Reagent which will result in the formation of a
reddish-brown colour precipitate. Hence, the reaction results in the formation of carboxylate
anion. However, aromatic aldehydes do not react to Fehling's Test which is why other
compounds did not result with any reactions.
 In performing Resorcinol Test, only formaldehyde produced a red precipitate at the junction
of two liquids. Resorcinol reacts with formaldehyde in alkaline medium at low temperature
already. The reaction products are mixtures of addition and condensation compounds which
react further to form high molecular compounds, mostly infusible and insoluble.

Formaldehyde is easily oxidized by an excess of oxidants to carbon dioxide and carbon

monoxide. A mechanism for formaldehyde oxidation is proposed which involves adsorption of
formaldehyde followed by catalytic decomposition to CO and H2 and oxidation of the surface
species. In this procedure, only acetone has no reaction while formaldehyde and benzaldehyde
turned green in color from orange. Formic acid, acetic acid, and benzoic acid produced green
liquid pigment.

Lastly, in performing iodoform, only acetone had reaction and turned yellow in color. The
rest of the compounds did not occur any reactions. Iodoform is a test for the presence of
compounds with methyl carbonyl group. The chemical reaction can be expressed in the
chemical equation: RCOR + 3I2 + 4NaOH  CHI3 + NaCH3COO + 3NaI + 3HOH

VII. SIGNIFICANCE OF THE EXPERIMENT

In handling and performing laboratory experiments, it is important to know the properties of

the various chemicals and compounds that we are dealing with. By means of knowing and
identifying their properties and composition, experimenters are aware and can prepare for
precautionary measures. Benzoic acid is non-toxic and is often stable under ordinary conditions.
Similarly, acetic acid is not harmful to human health. Formic acid, on the other hand, is the root
cause of methanol toxicity. Acetone, as well, is considered a hazardous waste material.
Breathing benzaldehyde can also irritate the nose and throat which can cause coughing and
shortness of breath. Lastly, formaldehyde is designated as a hazardous air pollutant.

Benzoic acid is most commonly found in industrial settings to manufacture a wide variety of
products such as perfumes, dyes, topical medications and insect repellents. Acetic acid which is
a dilute solution is used extensively as vinegar. The principal use of formic acid is as a
preservative and antibacterial agent in livestock feed. Common uses of Acetone include cleaner
for grease, oil, resin, ink, permanent marker, adhesive, and paint. Benzaldehyde is an aromatic
aldehyde used in cosmetics as a denaturant, a flavoring agent, and as a fragrance.
Formaldehyde is used in pressed-wood products, such as particleboard, plywood, and
fiberboard

VIII. RESOURCES

 New Jersey Department of Health. (2016, April). Hazardous Substance Fact Sheet:
Formaldehyde. New Jersey.

 New Jersey Department of Health. (2016, April). Hazardous Substance Fact Sheet:
Benzaldehyde. New Jersey.
 ICSC 0087 - acetone. (n.d.). Retrieved October 13, 2021, from
http://www.ilo.org/dyn/icsc/showcard.display?
p_card_id=0087&p_version=2&p_lang=en.

 Team, V. C. (2020, August 15). Tollen's Reagent. Benzaldehyde. Retrieved October 13,
2021, from https://www.vedantu.com/question-answer/benzaldehyde-gives-a-positive-
test-with-which-of-class-12-chemistry-cbse-5f37cbc00fb754474e250877.