Aldehyde oxidation

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Organic Chemistry 4e Carey

Chapter 17: Aldehydes and Ketones. Nucleophilic Addition to C=O

Nucleophilic Addition Reactions - Overview | Relative Reactivity | Reduction of Aldehydes and Ketones | Using Carbon Nucleophiles | Using Nitrogen Nucleophiles | Oxygen Nucleophiles | |

Oxidation Reactions

Chapter 17: Aldehydes and Ketones. Nucleophilic Addition to C=O

Oxidation of Aldehydes

Reaction type: Oxidation - reduction

Summary

• Aldehydes, RCHO, can be oxidized to carboxylic acids, RCO2H.
• Ketones are not oxidized under these conditions as they lack the critical H for the elimination to occur (see mechanism below).
• Typical reagents are aqueous Cr (VI) species:

Related Reactions OXIDATION OF ALDEHYDES Part 1:
Formation of the hydrate (mechanism) occurs first.
Part 2:
Now we essentially have an alcohol which reacts with the chromium species to form a chromate ester. Part 3:
A base (here a water molecule) abstracts a proton from the chromate ester, the C=O forms and a Cr species leaves. This is really an E2 elimination reaction. Note the importance of the original aldehyde H... if its' missing, no oxidation can occur.

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