Electron Pushing Exercise

To do this exercise, you will need to download and install the ViewerLite program. In this exercise, there are two reaction sequences for the following rearrangement. 

The two methods follow different pathways, but lead to the same result.  The first starts by protonation of the nitrogen and the second starts by protonation of the carbonyl oxygen. 

The basic approach is to allow electrons to flow from the place of greatest electron density to the place of least electron density. Generally positive things are attracted to negative things (like electrons). 

Your job is to draw each structure in each reaction sequence showing the electron flow for each step. The structures are shown with electron density mapping on the surface of the molecule that indicates relative electron density. You should cut and paste into Isis Draw, but you must draw in all non-bonding electrons. Arrange the atoms to clearly show the electron flows. The mouse must be in your hand for credit.

Method 1
    Structure 1
    Structure 2
    Structure 3
    Structure 4
    Structure 5
    Structure 6
    Structure 7
    All Structures
Method 2
    Structure 1
    Structure 2
    Structure 3
    Structure 4
    Structure 5
    Structure 6
    Structure 7
    Structure 8
    Structure 9
    All Structures