The Oxidation of Alcohols

  • DOI: 10.1002/chemv.201700026
  • Author: ChemViews
  • Published Date: 02 May 2017
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: The Oxidation of Alcohols

The oxidation of alcohols is an important reaction in organic chemistry. Primary alcohols can be oxidized to form aldehydes and carboxylic acids; secondary alcohols can be oxidized to give ketones. Tertiary alcohols, in contrast, cannot be oxidized without breaking the molecule's C–C bonds.





Oxidation Reactions

Alcohol Oxidation

During the oxidation, the orange dichromate ion is reduced to the green Cr3+ ion. This can be used to detect alcohols.




Reactive C–H Bonds

Alcohol Oxidation

([O] = Oxidizer)




Reagents for Alcohol Oxidation

For the oxidation of primary alcohols to aldehydes

  • Cr2O72– (dichromate)
  • CrO3/pyridine (Collins reagent)
  • Pyridinium chlorochromate (PCC)
  • Pyridinium dichromate (PDC, Cornforth reagent)
  • Dess–Martin periodinane
  • Dimethylsulfoxide (DMSO)/oxalyl chloride (Swern oxidation)
  • etc.


For the oxidation of secondary alcohols to ketones

  • Cr2O72– (dichromate)
  • CrO3/pyridine (Collins reagent)
  • Pyridinium chlorochromate (PCC)
  • Pyridinium dichromate (PDC, Cornforth reagent)
  • Dess–Martin periodinane
  • Dimethylsulfoxide (DMSO)/oxalyl chloride (Swern oxidation)
  • CrO3/H2SO4/acetone (Jones oxidation)
  • Aluminium isopropoxide/acetone (Oppenauer oxidation)
  • etc.


For the direct oxidation of primary alcohols to carboxylic acids

  • KMnO4 (potassium permanganate)
  • RuO4 (ruthenium tetroxide)
  • CrO3/H2SO4/acetone (Jones oxidation)
  • etc.

Sources

 

Article Views: 54497

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more

Follow on Facebook Follow on Twitter Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH