[zsinger]

All,
I have purchased all books recommended to me, and have read them all (Including the 1000+ page Klein's Advanced Organic Chemistry) in my 7+ year chemistry academic career up to now.  However, I still am having problems that my coworkers just don't have.  They are able to see molecular transformations much better than I.  I am good at the theorizing and I always understand it once they propose it, but its always someone else who thinks up a way to either achieve Umpuolong, a more reactive synthon, better chelation ideas, protecting group strategy, etc.  To the experienced chemists in this forum:  What was the single most important thing you have CONSISTENTLY done in your younger years as a chemist in order to correct this problem.  I know everyone hits a wall at some point, and breaching it separates the boys from the men.
          -Z

[orgopete]

I seemed to have done reasonably well with two approaches. One, I am very dogmatic. This doesn't take a lot of thinking. If you want to prepare something, write down all of the possibilities. If there is a bond you wish to make, there are three ways to do it, +-, -+, and **. If you begin to see which ones actually seem reasonable, some are a lot better than others. I also used this as a reaction searching strategy, either to find new chemistry or create it. Umpulong strategies fall out naturally.

The other part we can call, "look it up". It is one thing to theorize reactions, but your molecules will undoubtedly have context. There have been other similar reactions that have been tried in the past. It is helpful to know which chemistry is good chemistry and which is a prayer that you hope will be answered. If you are betting your career on one reaction, I'd avoid hoping your prayer will be answered.

When I was in industry, we had REACCS. What was good about it was that it was a filtered source of reactions. In my case, by being dogmatic, I wasn't afraid to strip away a lot of chemistry to try to find new reactions. That sometimes resulted in some pretty large hit lists. I'd look through all of them by-passing the familiar or similar looking for the unusual. All of this should prove to you that I used perseverance in lieu of intelligence.

That was my approach to create out of the box thinking.

[Irlanur]

How I see it: all the reactions you know are a toolbox. it's good to know the mechanism to all of them, but they are often practically irrelevant. so you need a view from further appart, just see what the reactions do. Once you have a reasonably big toolbox, think in "bigger steps".

To compare it with programming: at the beginning, you have to worry about how to exactly do a for-loop. then maybe you need to have two loops inside each-other and you have to think about the exact indexing. after some practice, you can easily do any number of connected loops with all kinds of checking and stuff.

It's the same in OC. e.g. you know reactions to make aldehydes from alcohols. and you know how to make alkynes from aldehydes. then you have to make the connections how to make an alkyne from an alcohol. Build "Brain-Highways" for these connections. of course you're faster then. the rest is pattern-recognition, and you can't do this by reading books, you have to exercise.

[zsinger]

Thanks guys.  Good advice.
     -Zack