Pictures of the Day 2-22-08

 

b-ketoacid Decarboxylation
b-ketoacids exist largely in a six-membered ring, hydrogen bonded conformation. Upon heating, the bonds rearrange as shown by the arrows above, creating an enol and CO2. The enol tautomerizes to the methyl ketone to complete the reaction. Note how the original hydrogen bond helps set up the molecule for the reaction by fixing the appropriate geometry.