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A possible competitive reaction is the “self-condensation” of two molecules of acetaldehyde. 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. with source
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The self-condensation of acetaldehyde is an aldol condensation reaction, which is catalyzed by bases. Slow addition of acetaldehyde to a benzaldehyde solution containing a base favors the formation of the desired benzaldehyde product over the self-condensation of acetaldehyde. This is because the slow addition ensures that the concentration of acetaldehyde in the reaction mixture is always low. As a result, the rate of the self-condensation reaction, which is dependent on the concentration of acetaldehyde, is significantly reduced. The benzaldehyde, being present in a higher concentration, can then react with the acetaldehyde faster.
Another method to combat the self-condensation of acetaldehyde is to use a different base. Bases like sodium hydroxide or potassium hydroxide are known to be strong bases and can promote aldol condensation reactions readily. Therefore, using a milder base such as sodium bicarbonate can reduce the rate of the self-condensation reaction, leading to a higher yield of the desired product.
Source:
Organic Chemistry, 10th Edition by Paula Yurkanis Bruice
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