Identify all of the different b-hydroxyaldehydes that are

Step 1 of 2

This exercise requires us to identify all of the different ? - hydroxyaldehydes that are formed when a mixture of benzaldehyde and hexanal is treated with aqueous sodium hydroxide. Recall that protons on carbons alpha to a carbonyl group are unusually acidic due to resonance stabilization of the resulting anionic conjugate base. This anion can attack electrophilic centers such as carbonyl carbons.

The two possible combinations are: deprotonation of hexanal followed by attack on benzaldehyde, and deprotonation of hexanal followed by attack on hexanal.

Benzaldehyde not having any alpha hydrogen so, it cannot form the carbanion.

With that in mind, we can now draw both ? - hydroxyaldehydes that are formed.