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Slow addition of the acetaldehyde to a benzaldehyde solution containing the base will often result in less self-condensation. Explain. Identify one other method that can be used to combat this competitive reaction. Include sources and page numbers
Accepted Answer
The slow addition of acetaldehyde to a benzaldehyde solution containing a base minimizes self-condensation because it ensures that the acetaldehyde reacts with benzaldehyde as soon as it is added. This is because the base promotes the formation of the enolate ion of benzaldehyde, which is highly reactive and prone to self-condensation. By adding acetaldehyde slowly, the enolate ion has a higher chance of reacting with acetaldehyde before it can react with itself.
One other method to combat self-condensation is to use a catalytic amount of a strong base. This strategy favors the formation of the enolate ion of benzaldehyde, which then reacts with the acetaldehyde. The strong base will quickly deprotonate the benzaldehyde, but the amount used will not be sufficient to promote significant self-condensation.
Source:
Vollhardt, K. P. C., & Schore, N. E. (2018). Organic Chemistry (9th ed.). W. H. Freeman and Company. (Pages 879-880)
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