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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 |

Oxidation Reactions

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

Oxidation of Aldehydes

oxidation of aldehydes
Reaction type:  Oxidation - reduction


oxidising reagents for aldehydes
Related Reactions
Part 1:
Formation of the hydrate (mechanism) occurs first.
oxidation of an aldehyde to a carboxylic acid

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.

The Baeyer-Villager Reaction

A Baeyer-Villager oxidation

Reaction type:  Oxidation -reduction via Nucleophilic addition


Baeyer-Villager reaction of a cyclic ketone
the O atom inserts on the more substituted side of the carbonyl In this example the primary ethyl group migrates in preference to the methyl group

Related Reactions

Step 1:
An acid/base reaction. Protonation of the carbonyl activates it while creating a more reactive nucleophile, the percarboxylate.
mechanism of the Baeyer-Villager reaction
Step 2:
Now the nucleophilic O attacks the carbonyl C with the electrons from the p bond going to the positive O.
Step 3:
Electrons from the O come back (this reforms the p bond of the C=O) and we migrate the C-C electrons to form a new C-O bond displacing the carboxylate as a leaving group.
Step 4:
Finally an acid/base reaction reveals the C=O and therefore the ester product.


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