Reddit reviews Frontier Orbitals and Organic Chemical Reactions

Mathematical approaches to "typical organic chemistry problems" are certainly possible (via quantum calculations etc.), but the problem is that they very quickly become very complex, and you need to make approximations for all but the very simplest molecules. At which point you might as well use the arrow-pushing rules-of-thumb anyway.

A limited approach that uses math to predict the course of reactions can be found in Fleming's book https://www.amazon.ca/Frontier-Orbitals-Organic-Chemical-Reactions/dp/0471018198 but that too, is just an approximation. And you will probably need three or four semesters of organic chemistry under your belt before it'll make much sense.

While it is a textbook, Ian Fleming's book (pirate it here ) might be what you're looking for. It doesn't really go into the 'cookbook' style cataloging of syntheses, which was what I hated the most about undergrad textbooks. Rather it tries to put a proper physics-based foundation to most of the o-chem you would have learned as an undergrad.

I'm a theoretical chemist (experiments and me didn't get on, last thing I did in a lab was stab myself in the finger with an air blower), so you may want to treat what I say with a pinch of salt.

However, I found that there's potentially quite a lot of nice stuff in trying to understand mechanisms and suchlike, rather than just having to rote learn everything. Maybe try to get hold of some books on physical organic chemistry or on some more MO-based stuff (e.g. http://www.amazon.com/Frontier-Orbitals-Organic-Chemical-Reactions/dp/0471018198).

Hope that helps.