Cannizzaro Reaction of Formaldehyde

2HCHO + NaOH → HCOONa + CH3OH

Descripción general

In the Cannizzaro reaction, two molecules of a non-enolizable aldehyde undergo disproportionation in the presence of strong base. One molecule is oxidized to a carboxylate salt while the other is reduced to an alcohol. Formaldehyde disproportionates to sodium formate and methanol.

Participantes

Rol Sustancia Coeficiente Estado
Reactivo Sodium Hydroxide NaOH 1 (aq)
Reactivo Formaldehyde CH₂O 2 (aq)
Producto Methanol CH₃OH 1 (l)

Ejemplo cotidiano

The Cannizzaro reaction demonstrates that oxidation and reduction can occur simultaneously between identical molecules (disproportionation).

Importancia industrial

La reacción cruzada de Cannizzaro del formaldehído con otros aldehídos produce polioles como el pentaeritritol, utilizado en resinas alquídicas y explosivos (PETN).

Propiedades

Tipo
Organic
Reversible
No
Energía
Exotérmico
ΔH
-60,0 kJ/mol

Reacciones relacionadas

Epoxidation of Alkenes (mCPBA) Swern Oxidation Oxidation of Secondary Alcohol to Ketone E2 Elimination (Dehydrohalogenation) Claisen Condensation (Ethyl Acetate) Aldol Condensation of Acetaldehyde Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Dehydration of Ethanol

Frequently Asked Questions

What is the equation for Cannizzaro Reaction of Formaldehyde?
The balanced equation is: 2HCHO + NaOH → HCOONa + CH₃OH.
What type of reaction is Cannizzaro Reaction of Formaldehyde?
Cannizzaro Reaction of Formaldehyde is a organic reaction.
Is Cannizzaro Reaction of Formaldehyde exothermic or endothermic?
Cannizzaro Reaction of Formaldehyde is exothermic (releases energy). The enthalpy change (ΔH) is -60.0 kJ/mol.