Cannizzaro Reaction of Formaldehyde

2HCHO + NaOH → HCOONa + CH3OH

Aperçu

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.

Participants

Rôle Substance Coefficient État
Réactif Sodium Hydroxide NaOH 1 (aq)
Réactif Formaldehyde CH₂O 2 (aq)
Produit Methanol CH₃OH 1 (l)

Exemple du quotidien

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

Importance industrielle

The crossed Cannizzaro reaction of formaldehyde with other aldehydes produces polyols like pentaerythritol, used in alkyd resins and explosives (PETN).

Propriétés

Type
Organic
Réversible
Non
Énergie
Exothermique
ΔH
-60,0 kJ/mol

Réactions associées

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.