Class Notes 1 - Hammond's Postulate

I should really call it the Hammond-Leffler postulate, but popularity can be influential in chemistry I suppose.

Class hasn't actually started yet, I have a couple of more weeks before I really have to worry about that.  But my (future) Advanced Organic Chemistry professor advised that we start studying a little early so we are not caught off-guard.  One of his biggest concerns is that students will be unprepared by the Hammond Postulate.  As a refresher for some of you out there, Hammond's postulate is that the transition state of a reaction will resemble the species closest to it in energy.  This makes sense, since most of the time when drawing transition state diagrams, the 'peak' is close on the reaction coordinate to whatever is higher in energy.  If the transition state is close in energy to the higher energy species, you can approximate this transition state as being the higher energy species.  This picture, courtesy of Master Organic Chemistry, summarizes it nicely:

As an example, an alkene being converted into a carbocation will have a transition state that resembles the higher energy carbocation.  

For me, this seems intuitive.  Heck, I'm fairly certain that we learned this in first semester OChem.  Why then is our professor concerned about us not being able to understand it?  From asking around, it seems that applying the postulate to actual reactions is where things are going to be tricky. 

What do you think?  Am I missing something here that makes this more complicated than I understand it to be?  Am I going to get my butt kicked this semester?  If this is all there is to it, I'm hoping that this is going to be the most difficult concept we learn.  Oh, who am I kidding.

-Woodward