Crossed aldol condensation is done between acetaldehyde and acetophenone by using NaOH as the base. So, here we can get 4 possible products. But which one would be the major?

I know that acetaldehyde will act as electrophile to which addition will occur. But what will act as nucleophile to give major product: acetaldehyde or acetophenone?

I don't have any solid reasoning whether acetaldehyde enolate or acetophenone enolate will give major product with acetaldehyde.

  • 1
    $\begingroup$ The so called 'cross aldol condensation' between a ketone and an aldehyde is actually called 'claisen-schmidt condensation' $\endgroup$ – Carrick Jan 11 at 7:22
  • $\begingroup$ And for the answer... it's generally easier for a nucleophile to attack on an aldehyde as compared to a ketone (steric and polar factors both can be used to explain that) $\endgroup$ – Carrick Jan 11 at 7:24
  • $\begingroup$ All the reactions leading to the 4 possible products are reversible so you will get the thermodynamic product. $\endgroup$ – Waylander Jan 11 at 7:32
  • $\begingroup$ @Carrick i know that neucleophile attack on aldehyde is better. But my question is which is better nucleophilic aldehyde or acetophenone enolate. $\endgroup$ – ATHARVA Jan 11 at 8:04
  • $\begingroup$ @Waylander But which out of the 4 is thermodynamic that is more stable product. $\endgroup$ – ATHARVA Jan 11 at 8:05

Your Answer

By clicking "Post Your Answer", you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.