Cagatan, Jay Marie B.

BSN

Experiment 7

Carbonyl Compounds: Aldehydes and Ketones

I. Introduction

The composition of aldehydes and ketones is very similar as they involve either C=O or the so-
called Carbonyl Group. At least one hydrogen is present in any C=O-connected aldehyde and
two organic alkyls with C=O-connected ketones. The aldehyde carbonyl group consisting of one
alkyl substituent and 1 hydrogen and the two alkyl substituents are referred to as ketone. These
two organic compounds are reacted by their carbonyl group, but since they are "susceptible to
oxidation" they can be separated.

Aldehyde carbonyl is always at the end of the carbon chain, while Ketone carbonyl may be
anywhere in the carbon chain. Both organic compounds are commonly present in nature. As this
carbonyl group is polar, there's a greater energy in aldehydes and ketones. The positive carbon
atom is caught by nucleophiles in the carbonyl group. Carbonyl groups can be subjected to
additional reactions. Since the hydrogen atom is bound to it, aldehydes are more oxidation-prone,
for example, loss of electrons. Ketones, however, really aren't oxidation tolerant to hydrogen
atom in their carbonyl group. Small aldehydes and ketones are easily dissolved in water but as
the chain increases in length, its solubility decreases.

For this experiment, several tests will be conducted to identify two unknown solutions where at
the end of this experiment, one of the solutions will be identified as aldehyde while the other one
is ketone. The test are Fehling's Test, Tollens' Test, Chromic Acid Test and Iodoform Test.

II. Objectives

At the end of the experiment, the students should be able to:

1. Carry out simple chemical test to distinguish of aldehydes and ketones

2. Described the difference and structure of aldehydes and ketone
 3. Study the properties of aldehydes and ketones.

III. Ap paratus& Chemicals

Chemicals Materials

• 6 M Sodium hydroxide • Test tube

• 3mL 0.1 M Silver Nitrate • Test tube rack
• 6 M Ammonium Hydroxide • Dropper
• 6 M Nitric Acid • Bunsen burner
• Carbonyl compound containing α-hydrogen • Erlenmeyer Flask
• Potassium Iodide • Wire Gauze
• 2mL concentrated sulfuric acid
•1000mL beaker
• 70% tap water
• 2mL Fehling’s solution
• Chromic acid solution
• Distilled water

• 0.5g potassium dichromate

IV. Procedures

A. Tollens’ Silver Mirror Test

1. In every test tube, ten drops of 6 M NaOH were added and the bottom part of the tube
was rinsed by swirling. The NaOH solution was left for 1 minute in the test tube and the
solution was thrown out in the drain.
2. Per test tube also has approximately 1 ml of 0.1 M AgNO3 solution. There was produced
a brown AgOH precipitate.
 3. It was also applied and swirled around 15-20 drops of 6 M NH4OH solution before the
brown precipitate dissolved completely. Until dissolved, the brown precipitate was
applied to the test tube several additional drops of 6 M NH4OH.
4. The test tube was also applied to three drops of aldehyde or ketone to be checked and
swirled gently into a mixture.
5. The test tube stayed unstöred for 5-10 minutes.
6. The remarks should also be documented. And for all the aldehydes and ketones studied,
the procedure has been repeated.
7. The contents of the tubes were removed from the waste bottle after the experiment.
8. The 6 M HNO3 tubes were added and properly disposed of in the waste bottle when
washed.

B. Fehling’s Test

1. 70 percent of tap water was filled with the 1000 mL beaker and it started to heat through
a bunsen brand.
2. A test tube was added with 2 mL of Fehling's solution.
3. The Fehlings' reagent was applied to five drops of the compound to be checked.
4. Even in a boiling water bath the tube is placed.
5. Changes existed for about 5 minutes.
6. The tubes' contents are in the bottle of waste.

C. Oxidation with Chromic Acid

1. A test tube was filled with two drops of chromic acid solution.
2. Into the test tube is inserted 6-8 drops of the compound being examined.
3. Well swirled and found some changed color within 1 minute.
4. The material of the test tube was dissipated properly in the waste bottle after the entire
procedure was carried out.

D. Iodoform Reaction

1. In the test tube, 1 mL 6 M NaOH has been introduced.

 2. In the test tube also were placed 5 drops of the compound to be tested.
3. In each test tube, three drops of iodine I2/KI were placed.
4. During the observation, the result was documented.
5. The substance of the waste bottle test tubes was disposed of.

V. Data & Results

A. Physical Property

Boiling
Compound Structure Odor Solubility Density
Point

Aldehyde Soluble in Less dense than

Pickle-like odor -19.5oC
(formaldehyde) water water

Ketone
Pleasan, sweet and Soluble in Less dense than
(propanone) 56oC
fruity water water

B. Oxidation Tests

Compound Tollen’s Fehling’s Chromic Acid Iodoform

Positive Positive Positive
Aldehyde Negative
(Silver mirror) (Orange-red precipitate) (Green coloration)
Positive
Ketone Negative Negative Negative (Yellow
precipitate)
VI. Analysis and Discussion

Physical Properties

The class of organic compounds which have a carbonyl group, namely a double bond (-C = O) of
carbon oxygen is aldehyde and ketone. Because in the carbonyl group they don't have any other
reactive groups, including –OH or –Cl, they seem to be very simple compounds. The presence of
carbonyl groups is strongly affected by the composition of aldehydes and ketones.

Methanal boiling points are -19o C and +21o C for ethanal. Researchers can say therefore that
the ethanal boiling point is comparable to room temperature. The boiling point of aldehydes and
ketones usually increases by the growth of molecular weight. The boiling point depends on the
intermolecular strength.

The solubilities of aldehydes and ketones in water are decreasing, but the length of the chain is
increasing. Aldehydes and ketones, which are of small size and mixed with water in nearly all
compositions, are methanal, ethanal and propanone.

Aldehydes and ketones are not capable of producing hydrogen bonds, but can provide hydrogen
bonds with water molecules and this constitutes the source of good solubility for aldehydes and
ketones. This may have to do with dispersion forces and interrelations between dipole and
dipole. In various industries, aldehydes and ketones are used for numerous purposes. They are
commonly used in polymers, perfume mixing and flavor manufacturing. They are extensively
used in the manufacturing of polymers, blending of perfumes and also as flavouring agents.

Chemical Properties

Chemically speaking, all aldehydes and ketones constitute carbonyl carbon, with identical
chemical reactivity. However, the hydrogen atom bonded to the carbonyl group makes aldehydes
highly vulnerable to oxidation. This is why these two groups of compounds are differentiated.
Quite few tests are helpful for identifying aldehydes from ketones.
 Tollen’s Test

Another useful method to differentiate aldehydes from ketones is the Tollens Test. The process is
produced by dissolving silver nitrate and sodium hydroxide to extract the red color and rendering
the solution colourless by placing ammonium hydroxide. Though aldehydes contain hydrogen
atoms, it allows oxidation convenient and thus the mirror image of the test tubes has been
formed. This may appear to be the silver substance in Acetaldehyde and Proprion aldehyde.
Therefore, these chemicals tested Tollen's reagent positively. The majority of compounds that
have been tested adversely are ketones because there has not been a reaction. There was no
change to the colorless solution due to Ketones being less susceptible to oxidation.

The Tollens Test is seen as a good outcome for the production of a solid silver precipitate.

A "silver mirror" is formed if an aldehyde is added in a tube incorporating the Tollens reagent.

If a ketone is inserted in a test tube containing the reagent of Tollens, however, there is no
precipitation as there is no reaction.

Fehling’s Test

Aliphatic aldehydes are separated from aromatic aldehydes by a Fehling’s test. Fehling solution
is prepared by adding a few drops of sulfuric acid dissolved in an aqueous solution or
pentahydrate copper sulfate. The Fehling Solution, however, is also formed by the combination
of sodium with sodium tartrate potassium.

The presence of a cuprous, red-precipitated oxide, which happened is a good outcome for the
Fehling’s test, if an aliphatic aldehyde is present.
The test of Fehling, however, results in aromatic aldehydes and ketones. And after the Fehling
solution was applied no red precipitate would appear.

Chromic Acid Test

A chromic test is conducted to differentiate between an aldehyde and a ketone. As chromic acid
is a potent oxidizer, aldehyde could readily be oxidised into a carboxylic acid. This reaction to
oxidation results in Cr6+ ions being reduced to Cr3+. In chromium sulfate, the appearance of
Cr3+ is seen. The green color of the Cr2(S04)3+ is in effect. The green color reflects the
oxidation of the aldehyde.

On the other hand, ketones are sensitive to reactions with oxidants like chromic acid due to
stability. Therefore in the presence of a ketone no discoloration of the reagent will occur.

Iodoform Reaction Test

A methyl ketone is used to differentiate from several ketones and aldehydes in the iodoform test.
The appearance of a yellow iodoform precipitate indicates that the solution is a methyl ketone.

The alpha proton, next to the carbon, is extracted under fundamental conditions. The reduction of
the alpha proton creates the alpha carbon nucleophilic, allowing it to strike a molecule of iodine.
The composition of iodine in alpha carbon increases the acidity of the two other hydrogen
substances and the two hydrogen substances are then struck by the base before all are replaced
by iodine. Then the bond between carbonyl carbon and iodine molecules is formed.
The iodoform test is also used for RCH3CHOH alcohol. Once an alcohol has this structure, it
may present the yellow precipitate iodoform, relatively similar principle of reaction occurs for
alcohols with methyl ketones which have the same structure.

VII. QUESTIONS:

1. What happens when an aldehyde gives a silver mirror when treated with Tollen’s reagent and
give red-brown precipitate when treated with Fehling’s solution? Explain how they are
formed using chemical equations.

In the Tollen test, the aldehyde oxidises into carboxylic acid with the activation of the
reagent. Followed by the reaction is the degradation of the silver ions in the Tollen's metallic
silver reagent, which produces a mirror on the test tube during experiments on a clean glass
tube.

RCHO + 2[Ag (NH3)2] OH → R-COONH4 + 3NH3 + H2O + 2Ag↓ (silver mirror)

However with regard to the Fehling’s test, the solution of Fehling reduces it instead to a red
precipitate that is Cuprous oxide when an aliphatic aldehyde is exposed to heat. Throughout
the reduction, the following reactions occur.
RCHO+2CU2+ +5OH-→RCOO− +Cu2O↓3H2O (Red precipitate)

2. Which of the carbonyl compound has produced iodoform? Which functional group must
present for this test to be positive?

A yellow precipitate including an antiseptic smell is the product of iodine, the base and a
methyl ketone. A pale yellow iodoform or triiodomethan precipitate is obtained after iodine
and sodium hydroxide are introduced with a compound that is either an alpha methyl ketone
or a secondaries with a methyl group. If an iodoformation test is positive, therefore
acetaldehyde must be the only CH3C=O aldehyde. It also tests positive for a number of
secondary alcohols found in alpha position by at least one methyl group.
3. Write a complete chemical reaction for the oxidation product formed when propanone reacts
with the Iodoform Reaction.

The complete chemical reaction for the oxidation product when a propanone reacts with the
Iodoform reaction is,
CH3COCH3 + 3NaOl  CH3COONa +2NaOH + CHl3

4. Which one of the tests performed in this experiment would be most useful in differentiating
butanal and benzaldehyde. Explain how you would interpret the results.

It is essential to conduct the tollen test for butanal and benzaldehydes. Since Tollen's reagent
could be recognized by both. Though an aldehyde, Tollen limits the reactant to a red-brown
Cu2O precipitate, however it creates a silver mirror.

VIII. Conclusion

In conclusion, the student was also able to find the various physical and chemical
properties of aldehydes and ketones. The students were able to obtain positives besides
Iodoform, which resulted in negative, using the following processes with aldehydes. With
regard to ketones, the findings were negative except for the iodine test, which provided a
positive result. Through all of the processes that are carried out, the student was also able
to dictate which test results would be good if compromised by reagents and which
compound mixture would not respond to each test. The objectives of the experiment
were achieved after the experiment because aldehydes and ketones had their physical
properties detected using their test samples. It is recommended to perform more tests
which will help identify the identity of the compound in order to prevent uncertainty in
deciding whether the compound is an aldehyde or a ketone.

IX. References
VIDEO:
https://youtu.be/GPoDMqWJTWA
SOURCES:

(n.d). Retrieved from

https://www.academia.edu/23664646/Experiment_Title_PROPERTIES_OF_ALDEHYDES_AN
D_KETONES_Subject_UDEC_1164_ORGANIC_CHEMISTRY_Course_BACHELOR_OF_S
CIENCE_HONS_BIOCHEMISTRY_Title_Properties_of_Aldehydes_and_Ketones

(n.d). Retrieved from

http://www.chemhaven.org/che102/lab/CHE102_E23_S12.pdf

(n.d). Retrieved from

https://chem.libretexts.org/Courses/Eastern_Mennonite_University/EMU
%3A_Chemistry_for_the_Life_Sciences_%28Cessna
%29/15%3A_Organic_Acids_and_Bases_and_Some_of_Their_Derivatives/
15.09_Hydrolysis_of_Esters

(n.d). Retrieved from

https://www.scribd.com/doc/248189422/Aldehydes-and-Ketones-Individual-Laboratory-Report

X. Documentation

Iodoform Test
Adding NaOH. Adding Iodine solution. Adding the solution to boiling water. Result
Tollen’s Test

Creating Tollen’s reagent with silver nitrate solution, NaOH, and ammonia solution.

Adding Tollen’s reagent. Adding the compound. Adding the solution to boiling water.
Result.

Chromic Acid Test

Preparing chromic acid reagent. Adding the reagent to the solution.

Result.

Fehling’s Test

Creating Fehling’s reagent with Fehling Solution A (dilute Cu2+ solution) and Fehlings Solution B
(alkaline solution of sodium potassium tartarate)
Adding the reagent to the solution. Adding the solution to boiling water. Result.