Sterically hindered ketones lacking alpha-hydrogens can undergo the Cannizzaro reaction.
the verdict
REFUTED
the evidence says no
refutedsupported
the weight of evidence
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Retrieved reference materials state that the Cannizzaro reaction is a disproportionation restricted to aldehydes, indicating that ketones do not undergo this reaction.
# Can substituted acetone undergo Cannizzaro reaction?
- Tags: organic-chemistry, reaction-mechanism, carbonyl-compounds
- Score: 5
- Views: 7,173
- Answers: 2
- Asked by: user80551 (410 rep)
- Asked on: Aug 21, 2013
- Last active: Jul 7, 2018
- License: CC BY-SA 4.0
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## Question
I know the Cannizzaro reaction takes place in carboxyl compounds without $\\alpha$-H with the regular examples being formaldehyde and benzaldehyde.
But can this reaction take place with say diphenylmethanone or di ter-butyl ketone (2,2,4,4-tetramethylpentan-3-one) or 2,2-dimethylpropanal ?
I couldn't find any examples of these compounds showing the cannizzaro reaction.
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## Accepted Answer — Score: 10
- By: Greg E. (12,001 rep)
- Answered on: Aug 21, 2013
As far as I'm aware, the Cannizzaro reaction can't occur with ketones, only aldehydes. The reaction mechanism involves the transfer of hydride from the former carbonyl carbon (of the tetrahedral intermediate resulting from hydroxide's nucleophilic addition to the carbonyl carbon), during which step the carbonyl reforms, yielding a carboxylic acid. Since a ketone, by definition, has no hydrogens bonded to the carbonyl carbon, it obviously ca
Cannizzaro reaction
The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non- enolizable aldehyde to give a primary alcohol and a carboxylic acid.
Cannizzaro first accomplished this transformation in 1853, when he obtained benzyl alcohol and potassium benzoate from the treatment of benzaldehyde with potash(potassium carbonate). More typically, the reaction would be conducted with sodium hydroxide or potassium hydroxide, giving the sodium or potassium carboxylate salt of the carboxylic-acid product:
2 C6H5CHO + KOH → C6H5CH2OH + C6H5COOK
The process is a redox reaction involving transfer of a hydride from one substrate molecule to the other: one aldehyde is oxidized to form the acid, the other is reduced to form the alcohol.
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## Mechanism
Animated reaction mechanism
The reaction involves a nucleophilic acyl substitution on an aldehyde, with the leaving group concurrently attacking another aldehyde in th
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