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.