Now for a surprising product, whose structure and stereochemistry can be determined by NMR. Normally, reaction of a symmetrical ketone such as acetone with an aromatic aldehyde and base gives a double aldol condensation product in good 体eld.
But in one particular case, the reaction between pentan一2-one and 4-chlorobenzaldehyde, a different product is formed. The mass spectrum shows that two alehydes have reacted with one ketone as usual, but that only one molecule of water has been lost.
Some of what we know about this compound is shown in the scheme