Action of an Oxidizing Agent on the Carbonyl Group

Baeyer’s test

We will find out what happens to samples that contains the carbonyl group when added with an
oxidizing agent. Note

Our samples are: acetic, formic, benzoic, and oxalic acid. Each will be placed separately in test tubes.

Add 1mL of 0.5% potassium permanganate to each tube, this will be the oxidizing agent for this
experiment. Then, will be heated in a water bath. Heating speeds up chemical reactions.

Potassium permanganate is an inorganic chemical compound with the formula KMnO4. It’s a salt that
contains K+ MnO4- ions, it is a strong oxidizing agent. It dissolves in water to give intensely purple
solutions. It reacts with unsaturated aliphatic hydrocarbons, but does not react with alkanes because
they are saturated (single bonds which are all taken) and aromatic hydrocarbons. If there is no reaction
you should see no color change. When it reacts with unsaturated aliphatics it produces MnO2 , a brown
precipitate also CO2 and H2O. When it is added to an alkene, the purple color slowly disappears and a
brown MnO2 precipitate forms. The appearance of the brown precipitate indicates a positive test for
unsaturation.

Purple color dilutes to light purple = SATURATED. Purple color disappears and brown ppt forms =
UNSATURATED

( Heat the four test tubes in a water bath. It should have this violet color) Let’s see if there is a reduction
of the permanganate.

As what I’ve said, if there’s a color change or when the dark purple color will turn to light pink
or even colorless, this will indicate that a reaction occurred; the oxidizing agent was reduced or
there was a reduction of the permanganate by taking electrons onto itself while the reactants are
oxidized.

(Why does potassium permanganate oxidize formic acid and oxalic acid, but has no reaction
with benzoic acid and acetic acid?)

The reactions were heated in a water bath (~70-80 °C). Oxalic acid had turned colorless

The same reaction could be said for formic, but with the formation of a brownish precipitate

For both the benzoic and acetic acid, they remained purple.

Since benzoic and acetic acid are aromatic compounds, it does not react with the Potassium
Permanganate.

Alkanes and aromatic compounds do not react with potassium permanganate.

Potassium permanganate reacts with oxalic acid in a classic reduction-oxidation reaction, in short
called an redox reaction and the end products are carbon dioxide gas which bubbles away and
colourless manganese ions and water are left behind. We carry out the reaction in two test tubes,
one of which is placed in hot water while the other one is placed in cold water. We see that the
solution in hot water decolourizes first. Thus, we see that heat speeds up the rate of a reaction.
While our conclusion is generally true there are exceptions to it. If we heat a chemical substance so
much that it loses its structure then we may not even get a reaction, An example of this is enzyme
catalyzed reactions which happen in a specific temperature range. Too much heat destroys the
enzyme structure and kills the reaction.

1. http://www.epa.gov/ogwdw/mdbp/pdf/alter/chapt_5.pdf
2. Abiko, Atsushi; Roberts, John C.; Takemasa, Toshiro; Masamune, Satoru, Tetrahedron Letters (1986),
27(38), 4537-40
3. Jefford, Charles W.; Wang, Ying, Journal of the Chemical Society, Chemical Communications (1988), (10),
634-5.
4. Carey, F.A.; Sundberg, R. J. Advanced Organic Chemistry
5. Downing, Donald T.; Greene, Richard S., Journal of Investigative Dermatology (1968), 50(5), 380-6.
https://laney.edu/cheli-fossum/wp-content/uploads/sites/210/2012/01/5-Reactions-of-
Hydrocarbons.pdf

http://myweb.liu.edu/lawrence/che4x/e2hcrxns.pdf