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Baeyer-Villiger Oxidation: Ketones to Esters Bronsted acid/base interaction: Carbonyl oxygen is protonated. This will generate a more reactive carbonyl.

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Presentation on theme: "Baeyer-Villiger Oxidation: Ketones to Esters Bronsted acid/base interaction: Carbonyl oxygen is protonated. This will generate a more reactive carbonyl."— Presentation transcript:

1 Baeyer-Villiger Oxidation: Ketones to Esters Bronsted acid/base interaction: Carbonyl oxygen is protonated. This will generate a more reactive carbonyl group

2 Baeyer-Villiger Oxidation: Ketones to Esters Nucleophilic Attack of the peroxy acid on the highly reactive carbonyl unit

3 Baeyer-Villiger Oxidation: Ketones to Esters Sigma bonding electron-pair migrates with the phenyl group to the electropositive oxygen centre. This in turn initiates reorganization of sigma- and pi- bonding electrons in the peroxy acid group. The PHENYL group migration is very reminiscent of the [1,2]-Methyl shift in carbocation rearrangements.

4 Baeyer-Villiger Oxidation: Ketones to Esters Positive charge on carbon is neutralized through the loss of the hydroxyl hydrogen as a PROTON

5 Baeyer-Villiger Oxidation: Ketones to Esters Phenyl acetate


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