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Oxidation of Alkanols

Key Concepts

Oxidising agents are reduced:

  • purple permanganate ion, MnO4-, is reduced to colourless Mn2+.

  • orange dichromate ion, Cr2O72-, is reduced to green chromium (III) ions, Cr3+.

  • NAD+ (a biological oxidising agent) is reduced to NADH

Animated Tutorial

Examples

Oxidation of a Primary Alkanol

1-butanol is a primary alkanol, the OH functional group is attached to an end carbon atom.
  H
|		   H
|		   H
|		   H
|		  
H- C - C - C - C -OH
  |
H		   |
H		   |
H		   |
H		  
Oxidation of 1-butanol by acidified dichromate solution:
  H
|		   H
|		   H
|		   H
|		  
H- C - C - C - C -OH
  |
H		   |
H		   |
H		   |
H		  
H+/Cr2O72-
    →    
  H
|		   H
|		   H
|		   H
|		  
H- C - C - C - C =O
  |
H		   |
H		   |
H		      
H+/Cr2O72-
    →    
  H
|		   H
|		   H
|		   OH
| 		  
H- C - C - C - C =O
  |
H		   |
H		   |
H		      

1-butanol		 H+/Cr2O72-
    →    
butanal		 H+/Cr2O72-
    →    
butanoic acid

In the presence of excess 1-butanol, the reaction mixture should change colour from orange to green.

Oxidation of a Secondary Alkanol

2-butanol is a secondary alkanol, the OH functional group is attached to a carbon atom which is itself bonded to two other carbon atoms:
  H
|		   H
|		   H
|		   H
|		  
H- C - C - C - C -H
  |
H		   |
OH		   |
H		   |
H		  
Oxidation of 2-butanol by acidified dichromate solution:
  H
|		   H
|		   H
|		   H
|		  
H- C - C - C - C -H
  |
H		   |
OH		   |
H		   |
H		  
H+/Cr2O72-
    →    
  H
|		       H
|		   H
|		  
H- C - C - C - C -H
  |
H		   ||
O		   |
H		   |
H		  
2-butanol H+/Cr2O72-
    →     		butanone

In the presence of excess 2-butanol, the reaction mixture should change colour from orange to green.

Oxidation of a Tertiary Alkanol

2-methyl-2-propanol is a tertiary alkanol, the OH functional group is attached to a carbon atom bonded to 3 other carbon atoms:
      H
|		      
  H
|		   H-C-H
|		   H
|		  
H- C - C - C -H
  |
H		   |
OH		   |
H		  
2-methyl-2-propanol will not react with acidified dichromate solution, so the reaction mixture will remain orange.
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Related AUS-e-TUTE Topics

Summary of Nomenclature

Naming Straight Chain Alkanes

Naming Branched Chain Alkanes

Naming Simple Alkenes

Naming Simple Alkynes

Naming Structural Isomers of Alkanes

Naming Structural Isomers of Alkenes

Naming Alkanols

Naming Haloalkanes

Carboxylic (alkanoic) Acids

Functional Groups

Combustion of Hydrocarbons

Halogenation of Hydrocarbons

Hydrohalogenation of Hydrocarbons

Hydration of Alkenes

Dehydration of Alkanols (alcohols)

Preparation and Naming of Esters (Esterification)

Substitution Reactions of Haloalkanes (alkyl halides)

Preparation and Naming of Polymers (Polymerization)

Properties and Uses of Alkanes

Properties and Uses of Ethene (ethylene)

Properties and Uses of Polythene (polyethylene)

 
 

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