Oxidation of Alcohols by Potassium Permanganate

Katie LaMontagne
Introduction
The purpose of this experiment is to further understand reactions of alcohols and classify whether they are

primary, secondary or tertiary1,2. Specifically in this experiment, we treated several alcohols with potassium

permanganate so that we could compare their reactivities and be able to describe its effects upon the substrate

structure1,2.

Literature states that according to the scale of oxidation levels established for carbon primary alcohols,

RCH2OH, are at a lower oxidation level than either aldehydes, RCHO or carboxylic acids RCO2H. When the

appropriate oxidizing agents are applied, primary alcohols will first be oxidized to aldehydes before converting to a

carboxylic acid4.

Primary Alcohols

Unlike other reactions we learned throughout this semester, oxidation of alcohols involve the alkyl group of

the molecule (the C-H bonds) of the hydroxyl-bearing carbon4. Secondary alcohols, which contain only one C-H

bond, will oxidize to ketones. On the other hand, tertiary alcohols, which do not have any C-H bonds attached to

the hydroxylic carbon, will oxidize only with the accompanying degradation of smaller fragments by cleavage of the

carbon-carbon bonds4.

Secondary Alcohols

Tertiary Alcohols

Permanganate Oxidation
 According to literature, the permanganate ion, MnO4- , will oxidize both primary and secondary alcohols in

either basic or acidic solutions. In primary alcohols the product normally is the carboxylic acid due to the fact that

the intermediate aldehyde is oxidized rapidly by permanganate4.

Table of Relevant Properties

Prelab Calculations
NONE

Materials

Test tubes Ethanol

Potassium Permanganate 2-propanol
Methanol 2-methyl 2-propanol

Data Tables

Test Tubes 1 2 3 4 5

Alcohol Control Methanol Ethanol 2-propanol 2-methyl 2-

propanol

Evidence of Color change Color change to Change in color. Very slight color
Reaction to a light a dark red / Turns a deep change to a
maroon color. dark maroon red wine color. darker purple.
color.

Reaction Yes Yes Yes No

(yes or no)

Observations
We began our experiment with 5 test tubes containing a control and also our 4 different alcohols:

Methanol, Ethanol, 2-propanol, and 2-methyl 2-propanol and added the potassium permanganate KMnO 4

to each test tube. We waited for roughly 5 minutes and observed some color changes amongst each

alcohol. 2-Propanols reaction was most apparent as it turned much darker compared to the other

alcohols. Methanol and Ethanol’s color change were very similar to each other and 2-methyl 2-propanol

did not really change at all because it did not react.

Calculations

NONE

Results, Analysis & Discussion

 In this experiment we tested different types of alcohols with potassium permanganate to determine

if there would be a positive oxidation reaction. Because of the way that alcohols will oxidize, our results

indicated that the tertiary alcohol would not readily react because the carbon bond that is attached to the

alcohol group does not contain a hydrogen bond. This was also one of the objectives in conducting this

experiment and answers the professors question that a hydrogen cannot be lost if it did not exist there in

the first place.

This was evidenced by the fact that the 2-methyl-2-propanol had little to no color change. When

we compared our results from the tertiary alcohol to that of the primary and secondary alcohols we used in

this experiment we concluded that oxidation did in fact take place within the methanol, ethanol, and 2-

propanol because of the physical changes in color that resulted.

Furthermore, my findings suggests that since the color of the solution progressively became darker

from left to right (1o > 2o) respectively, this further reflects the differences in oxidation between the

alcohols. This was to be expected because of the concept that oxidation occurs mostly with primary and

secondary alcohols (methanol, ethanol and 2-propanol) but not in tertiary alcohols (2-methyl-2-propanol)

because the hydrogen atom is absent.

As a result, we were able to conclude the order of reactivity from our experiment is as follows: 2-

propanol > ethanol > methanol.

Post-Lab Questions
1.

2.
Conclusion

In this experiment we learned that primary alcohols will first be oxidized into aldehydes and then to
carboxylic acids, therefore making them easier to oxidize compared to tertiary alcohols. Also that secondary
alcohols easily undergo oxidation to ketones. Our results indicated that 2-propanol, a secondary alcohol, was the
most reactive, followed by ethanol and methanol respectively. The least reactive was 2-methyl-2-propanol, a
tertiary alcohol. Potassium permanganate (KMnO4) is primarily used in the oxidation of alcohols because it is a
very strong oxidant that is able to react with many functional groups, such as secondary alcohols, 1,2-diols,
aldehydes, alkenes, oximes, sulfides and thiols. Under controlled conditions, KMnO 4 oxidizes primary alcohols to
carboxylic acids very efficiently.

References
1. North Campus, B. (n.d.). Organic Chemistry Laboratory Manual CHM2210L (Vol. 2). Pearson.
2. Betts, Dr., director. CHM2210 Oxidation. YouTube, 25 November 2020,
https://www.youtube.com/watch?v=v1IGldWsaWQ&feature=youtu.be
3. “PubChem.” National Center for Biotechnology Information. PubChem Compound Database, U.S. National Library of
Medicine, https://pubchem.ncbi.nlm.nih.gov/
4. “Oxidation of Alcohols.” Basic Principles of Organic Chemistry, by Marjorie C. Caserio et al., Benjamin,
1977.