Hey there,
Given the massive sizes of our organic chemistry classes, and given that our prof had supposedly been ordered not to bell any of our class marks, he often seemed to select the whackiest little reactions to put on an exam. In addition, he liked to test our understanding of concepts in addition to the rote memorization; therefore, the toughest part of orgo was to, in a relatively short period of time, attain a good grasp of the forces driving reactions, as well as a well-memorized armory of reactions.
On reading the above posts, all of the above approaches sound good. One key thing is to quickly determine which strategy works best for you. One approach that I took for memorizing reactions hasn't yet been listed, but I found it very effective. So effective, in fact, that one year later, when I went to revitalize my orgo knowledge for the MCAT, the reactions came back to mind extremely quickly, allowing a good bit of confidence and time-recouping during the Biological Sciences section of the MCAT.
The approach basically involves grouping all the reactions into families. So there is the family of alkane reactions (not very many), alkene reactions (there were 6 major types (halo-additions, water additions, oxygen additions, etc., with sub-types in each category), alkynes, aromatics, and so on. For each family I made sure that I could state the family name, give the number of reaction sub-types within each, and then systematically write the name of all the different types of reactions within it. I then made sure I could draw the specifics of each reaction, e.g., mechanism, reagents, etc., and would practice this by writing these schemes down over and over again. It is basically a top-down approach: start with the macro and end with the micro level of detail for each group.
It takes a lot of time to master this approach, but the paybacks are huge. I found that, on exams where I was given either a product or reactant or odd reagent, I could zip through those sections--obscure little reactions and all--really quickly. I'd just simply list the reactions at the beginning of the test, or most often than not, I'd recognize a weird reagent, e.g. the Raney nickel, and would be able to name the reaction, cold. The reactions were all stored "up there" and easy to obtain. On the MCAT, like I mentioned, when it came to studying the reactions (and you will have to know the reactions for the MCAT) they came back really quickly and I was able to answer a couple of the more odd, one-off discrete MCAT questions that dealt with those more unusual types of reactions--the naughty one that I found tucked in as a discrete was the Wittig (the tip-off being the phosphorus reagent).
Whatever approach you take, best of luck! 🙂
Kirsteen