Cannizzaro Reaction of Formaldehyde

2HCHO + NaOH → HCOONa + CH3OH

Overview

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

Role Substance Coefficient State
Reactant Sodium Hydroxide NaOH 1 (aq)
Reactant Formaldehyde CH₂O 2 (aq)
Product Methanol CH₃OH 1 (l)

Everyday Example

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

Industrial Importance

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

Properties

Type
Organic
Reversible
No
Energy
Exothermic
ΔH
-60.0 kJ/mol

Related Reactions

Aldol Condensation of Acetaldehyde Amide Formation (Acetic Acid + Ammonia) Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Bromination of Ethylene Buchwald-Hartwig Amination Catalytic Hydrogenation of Ethylene Claisen Condensation (Ethyl Acetate) Condensation Polymerization (Nylon 6,6) Cope Rearrangement

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.