You want to know the mechanism for any reaction. In undergrad chemistry I would work problems, write out mechanisms, and use good flashcards (so a reaction that will get you to identify stereochemistry, regiochemistry, selectivity, etc.). For alkenes, 1-methycyclohexene is an excellent substrate for your flashcards.
My graduate advisor recommends 3 flashcards for a reaction. One is your standard starting material plus reagents with the product on the back of the card, the second is blank plus reagents gives product (so you supply the starting material), and the final one is starting material with a reaction arrow to product and you supply the reagents.
I know some students have really liked to write out reaction maps on paper that has say an alkene at the center and radiating from it are all the reactions you know that work on an alkene. That can help when you get to retrosynthesis in OChem 1.
But for each reaction you should know what the reactant type is (alkene, alkyne, alcohol, etc.), what the reagent is, and what the product is going to be. Product prediction comes from the mechanism and thats going to determine the regio and chemoselectivity of a reaction. You want to be able to realize that this reaction is a hydroboration so it gives this product, this reaction is a lindlar hydrogenation of an alkyne so I should get this and know why for that reaction.
Really though the best advice is that O-Chem is not a course that lends itself to cramming. It can absolutely punish poor study habits.