Chem 242 @ Dickinson

Imines and Enamines

Today we slid sideways into nitrogen nucleophiles reacting with C=O. We used the alcohol reaction as a template (protonate, add nucleophile, proton dance....) until the end when we can either lose a proton from nitrogen to form an imine or from a carbon to form an enamine. The deciding factor is the nature of the starting amine -- two hydrogens on the N will lead to an imine and only one hydrogen will lead to an enamine. We then saw how a special case of the imine reaction could be used to reduce a C=O to two separate C-H bonds (the Wolff-Kishner reaction).

At the end we broke up into groups for the first time and worked on acetal formation using a single equivalent of a diol rather than two equivalents of alcohol. An offer of a point and a half bonus on the exam led to an amazing display of hard work.

posted by DCChem @ 9:32 AM