Chapter 2: Aldehydes and Ketones

2.9 Baeyer-Villager Reaction

Baeyer-Villager reaction is the oxidation of an aldehyde or ketone by applying peroxycarboxylic acid as the oxidizing agent. In Baeyer-Villager reaction, the aldehyde is oxidized to carboxylic acid, and the ketone is oxidized to an ester. A couple of examples are given in Fig. 2.9a.

 

Fig. 2.9a Baeyer-Villager reaction examples

Peroxycarboxylic acid is a strong oxidizing agent, which has the peroxy group O-O. A common peracid used for Baeyer-Villager reaction is m-chloroperoxybenzolic acid, or mCPBA.

 

Fig. 2.9b The structure of mCPBA

The mechanism for Baeyer-Villager reaction is shown in Fig. 2.9c.

 

Fig. 2.9c Mechanism for Baeyer-Villager reaction

The group (R’ in the mechanism in Fig. 2.9c) migration is the key step in the mechanism. Different group has different tendencies for migration. It is shown from studies that the aptitude for migration is: H > Ar > 3° > 2° > 1° > methyl. For aldehyde, H migrates and results in carboxylic acid. For ketone, the migration group R’ will be the OR’ in the ester product.

 

Examples

Show the product of the following reactions.

Answers:

 

 

 

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