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Abstract

Introduction

Methodology

Results

Physical Properties of Acetaldehyde

Description on the product

Percentage yield

Theoretical yield

Actual yield

% Error

Chemical Properties of Acetaldehyde

Schiff’s Test

The colour of the solution turns light pink

Tollens’ Test

Silver precipitate is formed and eventually a silver mirror is formed

Sodium Bisulfite Addition

Resin Formation

Fehling’s Test

The colour of the mixture has changed from blue into red. A brick red precipitate is
formed.

Oxidation with dilute Potassium Permanganate

Discussion
Questions

Write a complete reaction for each of the following tests performed in the experiment and name
the organic product formed in each solution.

a. Schiff’s test
Schiff’s Test is done in order to distinguish an aldehyde from a ketone. The solution to be
used, the Schiff’s reagent, is produced by the reaction of a dye such as pararosaniline
with sodium bisulfite.

The appearance of a magenta color in the solution is regarded as the positive result for the
Schiff’s Test. This positive result is expected for aldehydes.

b. Tollen’s test

The Tollens’ Test is another useful tool in distinguishing aldehydes from ketones. It is
prepared by mixing silver nitrate and sodium hydroxide, and adding ammonium hydroxide to
remove the red precipitate and make the solution colorless. However, it is not usually done in the
laboratory due to its explosive character, and health risks due to the production of silver upon the
completion of the experiment.

For the Tollens’ Test, the formation of a solid silver precipitate is regarded as a positive result.

When an aldehyde is placed into a test tube containing Tollens’ reagent, a “silver mirror” is
produced.
c. Sodium bisulfite solution
Sodium Bisulfite Test is used to determine if an unknown compound is an aldehyde or an
aliphatic methyl ketone. If the unknown substance is either of the two aforementioned, a
white precipitate is formed.

Due to the nucleophilic nature of the bisulfite ion, it attacks the aldehyde or methyl
ketone by breaking the π bond of the carbon-oxygen double bond. The bisulfite ion then
attaches itself to the original carbonyl carbon to form the bisulfite addition compound.

d. Fehling’s test
Fehling’s Test is done to distinguish aliphatic aldehydes from aromatic aldehydes.
Fehling’s Solution “A” is prepared by adding a few drops of concentrated sulfuric acid to
an aqueous solution of copper sulfate pentahydrate. On the other hand, Fehling’s Solution
“B” is prepared by mixing sodium hydroxide with potassium sodium tartrate.

A positive result for the Fehling’s Test is the appearance of a red precipitate, cuprous
oxide, which happens when there is a presence of an aliphatic aldehyde.

e. Resin Formation

The reaction involves an aldehyde enolate reacting with another molecule of


the aldehyde. The products of these reactions are β-hydroxyaldehydes or aldehyde-
alcohols = aldols and the reaction is known as aldol reaction or aldol condensation.The
simplest aldol reaction is the condensation of ethanal.

The mechanism will be as follows:


*

 Can use either NaOH or KOH

In a base catalyzed aldol condensation, the mechanism will be as follows:

1. Deprotonation of alpha carbon.


2. Nucleophilic attack on another carbonyl carbon.
3. Protonation of Oxygen atom.

f. Oxidation with dilute potassium permanganate

Potassium permanganate is a strong oxidizing agent used to test the presence of an aldehyde
or a ketone.

If the compound present is an aldehyde, it will be readily oxidized by the potassium


permanganate into a carboxylic acid due to the presence of the hydrogen atom bonded to the
carbonyl group. Since the reaction is a redox reaction, Mn 7+ will be reduced to Mn4+. Mn4+ is
present in the solution as manganese dioxide, which gives the solution a brown color. The
presence of the brown color is regarded as the positive result for the experiment. (2)

+ MnO2

Why do you have to collect acetaldehyde in an ice bath?

Acetaldehydes are extremely volatile and a fire hazard. Ice bath can reduce the pressure
buildup.

Conclusion

The objectives of this experiment were met after the experiment. The acetaldehyde was
being able to be characterized by its chemical properties using the six experiments.
(insert some part of some results and discussion)

Some deviations on the results from the theoretical may be due to the impurities present
and errors while synthesizing acetaldehyde via organic oxidation reaction.