Saturday, 5 September 2020

Oxidation of Alcohols

Primary and secondary alcohols (only) are able to undergo oxidation. The most common oxidants for alcohols are:

  1. Acidified potassium permanganate (H+/MnO4-)
  2. Acidified potassium dichromate (H+/Cr2O72-)
In both primary and secondary alcohols, the observations for each oxidant are the same, but the organic products are different. There is no reaction with tertiary alcohols.

OBSERVATIONS
Permanganate: the purple colour disappears (it is reduced to Mn2+ ions)
Dichromate: when heated, the orange colour becomes green/blue (it is reduced to Cr3+ ions)

ORGANIC PRODUCTS
Primary Alcohol
In both cases, a primary alcohol is first oxidised to an aldehyde:


If we wanted to stop the reaction at this point (because we want the aldehyde but not the carboxylic acid, we would use apparatus called distillation. This works because the aldehyde has a lower boiling point than any of the reactants, so distills away when it is produced:

SOURCE: https://www.123rf.com/visual/search/80631818

The aldehyde is then further oxidised to a carboxylic acid:


Reflux is used to ensure that all reagents fully react. The boiling point of the carboxylic acid is too high for it to escape out the top of the condenser:


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