Reduction reactions in organic chemistry

Reduction reactions in organic chemistry

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Cannizzaro reaction: mechanism using the example of benzaldehyde

The disproportionation of an aldehyde into the carboxylic acid and the corresponding alcohol according to Cannizzaro is base-catalyzed. In the first step, a hydroxide ion is added to benzaldehyde.

In the second step there is a hydride transfer from the carboxylate ion to another benzaldehyde molecule. A hydride ion is usually a very poor leaving group, but the aldehyde, which is a Lewis acid, makes this hydride transfer possible. Presumably, therefore, the hydride transfer of the hydrogen atom to the carbonyl carbon and of the proton to the carbonyl oxygen takes place simultaneously, so that no free hydride occurs as an intermediate stage during the reaction.

The Cannizzaro reaction is a redox reaction, in the following example one benzaldehyde molecule is oxidized to benzoic acid, the other is reduced to benzyl alcohol.

Video: Organisk kemi repetition (July 2022).


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