Organic Chem II Lab Hinal Joshi

2/2/17
Experiment 16
Oxidation of Toluene

I. Introduction
In this experiment Toluene was oxidized with a powerful oxidizing agent,
potassium permanganate. Potassium permanganate will help oxidize the alkyl side
chain to a carboxylic acid as long as there is at least one hydrogen attached to allow
for the oxidation process to proceed. The length of the carbon chain in the alkyl side
chain is not important because it will be oxidized to its last carbon, which will be the
carbon in the carboxylic acid. The toluene will yield the benzoic acid as the final
product formed from the oxidation.

C6H5CH3 (toluene (aq) + 2 KMnO4(aq) → C6H5COOK(aq)+ 2 MnO2(S) + H2O(aq)+

KOH(aq)

Above is the chemical reaction, which will occur when toluene is oxidized with
potassium permanganate

II. Results
Name: Molar Mass:
Mass of filter paper: 0.174 g Actual Yield (g):
Theoretical Yield (g): Percent yield:
Melting Point: Chemical Formula:

III. Conclusion
Potassium benzoate is soluble in water and benzoic acid is not very soluble in
water. The addition of the hydrochloric acid decreased the solubility of the benzoic
acid even more. So it was important important to have vigorous stirring through
out the experiment to allow for the potassium permanganate to mix with the
toluene. Vigorous stirring allowed for any reagent or solvent that was on the top or
bottom to mix together and the heating allowed for the reaction to occur sooner.
This was an over all exothermic reaction so cooling was also essential. In the end,
the actual yield of the product was and the percent yield was . This was a
good oxidation experiment to learn how potassium permanganate is a strong
oxidizing agent. If there was any loss of product, it is possible to recover which we
did by washing and vacuum filtration. If over oxidation did occur, this may have
been a reason for a smaller percent yield.
Organic Chem II Lab Hinal Joshi
2/2/17
Changes: If we used excess potassium permanganate, it would have increased the
contact area when refluxing which would then decrease the total amount of time to
reflux.
Problems: There could have been an effect on the percent yield if the solution was
not acidified properly when adding the oxalic acid so that all the excess potassium
permanganate was destroyed properly.

IV. Questions

1. The earlier definition of oxidation is that organic molecules oxidation is a process

by which carbon atoms gains bonds to more electronegative elements, most
commonly to oxygen. There is a loss of hydrogen and gain of oxygen.

2. Reflux is a technique involving the condensation of vapors that come down as

liquid in this entire system it initially evolved from. It prevents the loss of the
solvent and the volume constant. It is used during distillations or to sometimes
supply energy for reactions, which were performed during heating conditions for
prolonged periods. Many organic reactions are very slow and can take an extended
period of time to have any effect or initialize yielding a product so heating the
reaction increases the rate of the reaction.

3. Vigorous stirring is important in the reaction because it allows for greater

interface between the organic molecule and water if the molecule is insoluble. The
oxidizing reagent in this experiment, KMnO4, can mix into toluene to allow for all of
constituents in the species to mix if it is at the bottom or the top of the flask. The
heat can also be distributed equally if the vigorous stirring commences through out
the reaction.

4. a. Benzoic acid

b. terephthalic acid

c.benzene- 1,2,4 tricarboxylic acid

5. C6H5CH3 (toluene (aq) + 2 KMnO4(aq) → C6H5COOK(aq)+ 2 MnO2(S) + H2O(aq)+ KOH(aq)