Cannizzaro Reaction in Organic Chemistry

By
Anne Marie Helmenstine, Ph.D.
Anne Marie Helmenstine, Ph.D.
Chemistry Expert
  • Ph.D., Biomedical Sciences, University of Tennessee at Knoxville
  • B.A., Physics and Mathematics, Hastings College
Dr. Helmenstine holds a Ph.D. in biomedical sciences and is a science writer, educator, and consultant. She has taught science courses at the high school, college, and graduate levels.
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Updated on November 05, 2019

Cannizzaro Reaction

This is the general form of the Cannizzaro reaction.
This is the general form of the Cannizzaro reaction. Todd Helmenstine

The Cannizzaro reaction is a redox disproportionation of aldehydes to carboxylic acids and alcohols in the presence of a a strong base.

The second reaction uses a similar mechanism with α-keto aldehydes.

The process is a redox reaction in which a hydride is transferred from one substrate to another. One of the aldehydes is oxidized to yield an acid, while the other is reduced to yield an alcohol. The Cannizzaro reaction sometimes produces unwanted byproducts in reactions involving aldehydes in basic conditions.

This is the crossed Cannizzaro reaction.
Read More
Crossed Cannizzaro Reaction
By Anne Marie Helmenstine, Ph.D.

History

The Cannizzaro reaction takes its name from its discoverer, Stanislao Cannizzaro, who first achieved the reaction in 1853. Cannizzaro treated benzaldehyde with potassium carbonate (potash) to obtain benzyl alcohol and potassium benzoate. While Cannizzaro used potassium carbonate, the use of potassium hydroxide or sodium hydroxide is more common.

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Helmenstine, Anne Marie, Ph.D. "Cannizzaro Reaction in Organic Chemistry." ThoughtCo, Feb. 16, 2021, thoughtco.com/illustrated-cannizzaro-reaction-608567. Helmenstine, Anne Marie, Ph.D. (2021, February 16). Cannizzaro Reaction in Organic Chemistry. Retrieved from https://www.thoughtco.com/illustrated-cannizzaro-reaction-608567 Helmenstine, Anne Marie, Ph.D. "Cannizzaro Reaction in Organic Chemistry." ThoughtCo. https://www.thoughtco.com/illustrated-cannizzaro-reaction-608567 (accessed April 20, 2024).