The reaction of 1,2-diols (vicinal diols) with periodic acid (HIO4) is known as Malaprade oxidation. It involves the oxidative cleavage of the carbon-carbon bond between the two hydroxyl groups.
- Mechanism: The reaction proceeds through a cyclic periodate ester intermediate.
- Product Prediction: The bond between the carbons bearing the -OH groups breaks. Each -OH group is converted into a carbonyl group (C=O).
A primary alcohol group (−CH2OH) becomes Formaldehyde (HCHO). A secondary alcohol group (−CHROH) becomes an Aldehyde (RCHO).
- A tertiary alcohol group (−CR2OH) becomes a Ketone (R2CO).
- Application: Ethylene glycol has the structure HO−CH2−CH2−OH. Both carbon atoms are part of primary alcohol groups. Therefore, the cleavage yields two molecules of Formaldehyde (2HCHO).
Reaction: CH2OH−CH2OH+HIO4→2HCHO+HIO3+H2O.