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15.20: C–C Bond Cleavage: Retro-Aldol Reaction

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Organic Chemistry

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C–C Bond Cleavage: Retro-Aldol Reaction

15.20: C–C Bond Cleavage: Retro-Aldol Reaction

The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.

In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.


Figure 1. The deprotonation of a β-hydroxy ketone to form an alkoxide ion.

Figure 2 shows the second step, which involves the cleavage of the carbon–carbon bond to yield a ketone molecule and an enolate ion.


Figure 2. The formation of an enolate ion.

Finally, as illustrated in Figure 3, the enolate ion is protonated to form the second ketone molecule.


Figure 3. The protonation of enolate generates a second ketone.

Similarly, the β-hydroxy aldehyde in the presence of a base undergoes the retro-aldol reaction to produce two aldehyde molecules.


C&C Bond Cleavage Retro-aldol Reaction Aldol Product Acidic Conditions Basic Conditions Carbon-carbon Bond Cleavage Carbonyl Compounds Mechanism Of Reaction Alkoxide Ion Deprotonation Hydroxy Ketone Enolate Ion Protonation β-hydroxy Aldehyde Base

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