[macman104]

So I'm taking a course called Organic Reaction Mechanisms.  But really we're basically covering tons of reactions to get exposure and prep for the next course which is Tactics in Organic Synthesis.  Anyway, this is a post that comes too late to help me for tomorrow, but hopefully I'll get some advice for the next big exam.  Tomorrow I have an exam, and it could be on any of the reactions we've covered so far (there's 94 in that list).  I've included the list of reactions we've "officially" covered, however any sophomore organic is pretty much fair game too (this part worries me less).

Anyway, I need some advice on how to go about storing all of this information.  Not so much storing, but how do I go about organizing it in my brain so that it's manageable? 

So far I've made basic flashcards for most of the reactions, and I'm going to finish that up, but memorizing 90-some reactions (and more to come as we work our way through the Named Organic Reactions book) is not reasonable/feasible.

Thoughts?  Also apologies for being so verbose (it's just how I write).

[agrobert]

If you are required to give an example or name a reaction from an example it really is memorization.  Although it is useful when studying to write the reaction name then do some example mechanisms followed by the name again.  After reading your list I know most of them in a general sense  but this is now in my senior year in Chemistry with an emphasis on organic/synthesis.  Tests for these classes usually test the most useful and applicable reactions.  For example one-carbon homologation (there is really no faster way w/o circular chemistry than the Arndt-Eistert reaction) and of course you can't forget Diels-Alder, Aldol, and Baldwin chemistry.  C-C bond formation is essential.  Most questions will involve C-C bond formation.  Oh yea, Swern followed by Wittig is key.

[macman104]

If you are required to give an example or name a reaction from an example it really is memorization.

Yea, he does usually give a few give an example of each of the following reactions, which I fail miserably on, since I don't usually remember the name.  Then the other part of the exam is usually a reactant and reagents and just "finish the reaction".  I typically do decent on those.

C-C bond formation is essential.  Most questions will involve C-C bond formation.

Yea, since sophomore organic and throughout everyone of this professor's courses, he calls them the "money-makers".

To illustrate part of the issue, in class we were talking about the Darzen Reaction which has an alpha-chloro carbonyl.  He asked "where else do we see alpha-halogen carbonyls in a reaction?".  I had no idea, but simply trying to shuffle through all of the reactions I knew about in my head was impossible, hence my desire to find a way to "organize" them.

[agrobert]

That would be the Favorskii rearrangement

http://en.wikipedia.org/wiki/Favorskii_rearrangement

Trying to organize reactions in such a way would really be more confusing.  Honestly I think it is useless to know reactions by name if you really don't understand the chemistry.  As well, just because you have a ring systems with an alpha halide to a carbonyl doesn't mean a Favorskii rearrangement is always plausible.  Knowing your foundational chemistry will tell you what side reactions to expect and possibly you will discuss the effect of ring size on this reaction.  And in general once you know the chemistry you don't really have to memorize the name because it should already be jammed in your brain (not by choice).  You seem to understand the majority of your chemistry and should do fine.  Look at it this way, all of the problems you miss on this test you surely will never forget again.