Frequently Asked Question

Questions asked by users might not always be phrased in the clearest way.

The crossed aldol condensation of acetaldehyde with benzaldehyde is aided by the fact that benzaldehyde bears no α-hydrogens. However, a possible competitive reaction is the “self-condensation” of two molecules of acetaldehyde. Explain. Identify one other method that can be used to combat this competitive reaction.

Accepted Answer

The crossed aldol condensation of acetaldehyde with benzaldehyde favors the desired product because benzaldehyde lacks α-hydrogens, preventing its self-condensation. Acetaldehyde, however, possesses α-hydrogens, leading to a competing self-condensation reaction, forming aldol products of acetaldehyde. To minimize this side reaction, one can utilize a large excess of benzaldehyde, driving the reaction towards the desired crossed aldol product. This approach ensures that acetaldehyde is more likely to react with benzaldehyde than with itself.


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