I think you're approaching organic chemistry the wrong way. What's important is top-down processing - knowing which connections and disconnections to make and when to make them - not bottom-up processing - memorizing the reagents and trying various combinations in a synthesis. I award most points allotted if a student can make the right connections in a synthesis even if they don't know the specific reagents to do so. In research, you always go and look them up. There's no point in memorizing all the reagents and solvents needed because now, with the power of search engines and databases, we can find any known reaction we want with just a click of a button - all reagents, solvents, and procedures included!
I see can how organic chemistry can be difficult if you approach it by memorizing all the possible reactions you learn and what reagents you need for them. But organic chemistry actually is very mathematical. We just don't teach it that way because pre-meds tend to hate math and organic chemistry, for some reason, has just become a pre-med class. Physical organic chemistry is usually taught as an upper-level, if not graduate, course. It deals with the often complex rates you see in organic reactions, kinetic isotope efffects, Hammett plots, the Hammond postulate, etc.