Chem 242 @ Dickinson

The Mixed Aldol

Today we saw how to do an aldol reaction with two different starting materials, instead of two different molecules of a single compound serving as nucleophile and electrophile. The trick here is to make sure that only one of the starting materials will be deprotonated by the base. This is carried out by either 1) making sure that only one of the starting materials has an acidic proton or 2) having enormous differences in acidity if both have acidic protons. We looked at examples of both strategies.

We also looked at intramolecular versions of aldol processes and spent some time learning how to draw the products of the ring-forming reactions. An important point here is that not all ring sizes are easily made; we are essentially reduced to making five- or six-membered rings.

posted by DCChem @ 11:16 AM