Aldehydes and Ketones – Part 2 | Organic Chemistry 3

Additional reactions of aldehydes and ketones are studied in this chapter: deoxygenation of carbonyls, addition of cyanide, Wittig reaction, Baeyer-Villiger oxidation

Deoxygenation of the Carbonyl Group

 

  1. Synthesis of a hydrazone:


     
  2. Wolff-Kishner reduction:



    Mechanism:

Addition of Hydrogen Cyanide


Mechanism:

Wittig Reaction


Mechanism:

  1. Preparation of the phosphorus ylides:


     
  2. Wittig reaction:

Baeyer-Villiger Oxidation


Mechanism:

Oxidation by peroxycarboxylic acids

 

With asymmetric ketones, esters can be selectively formed by migration of only one of the substituents. Migratory aptitudes in the Baeyer-Villiger reaction: Methyl  <  Primary alkyl < Phenyl ~ Secondary alkyl < Tertiary alkyl