Organic help

Hi all~ I’m hoping some of you organic “geniuses” can help me out there. I work very hard in my class, do well on the homework and supplemental problems, but when it comes to the exam I still seem to be mixing everything up. I understand the concepts fine, but I’m having trouble applying my knowledge when I don’t have my books and time to slowly think it all through. What I think I need is some sort of organizational schemes for reactions and syntheses that I can memorize easily and then run through my head checking off things whenever I’m presented with a reaction or synthesis. Ie…if it’s a primary molecule and reacts with such and such, it’s going to form this sort of product, etc. Does anybody know where I can access something broken down in this manner or how to go about making one for myself? My prof has absolutely no suggestions other than all of the stuff I’ve already been doing . Any ideas?
–Jessica, UCCS

Hey Jessica,
We, too, recently got to the mega-reaction chapter. After working through about three reactions in the chapter, I realized I had to find a way to summarize all of the information in a way that was meaningful to me if I were to be able to keep all of them straight.
I ended up making a table for myself (as a Word doc–I’m anal and needed for it to be extremely neat and organized–comes from my research/publications background).
One column has the reaction type, then the solvent/substrate considerations with some examples, the next column has the mechanism (protonation of double bond, nucleophilic attack by water…), the next column has the product, and the last column lists any stereochemical considerations.
Putting this together was instructive not only in relearning the theory behind all of the problems I had just done, but illustrated how one substrate would give you a cis diol, whereas another will give you a trans diol. I didn’t catch that just chugging through the sections.
After putting this together, I did through additional problems at the end of the chapter, identifying which reactions I could do cold, and which were tougher for me to do. So I practiced the latter until there were only like one or two I really had to think about–the rest were just instant reactions either to the product or the solvents/substrates.
That’s what worked for me. Perhaps something similar would help you keep everything straight?
Good luck!

Thanks for the suggestion Vera. I think I’ll try it. (I don’t know what a diol is yet, but I’m sure we’ll get there lol).
My boss (I work for the head of the chem dept who is also one of the orgo profs) is also going to sit down with me and the past exams and see if we can figure out what it is I’m truly missing. My own prof is absolutely no help. He just keeps saying well i’ve told everyone what they need to do (ie. memorize the rxns). Problem is I did have them memorized before the exam, but still messed them up during the exam. Plus memorizing the simplest alkenes and alkynes is way different than applying them to these really complex molecules we’re supposed to. Something just isn’t quite clicking yet, and obviously my prof’s methods aren’t helping yet he’s totally unwilling to explore any other options with me. Thankfully my boss is lol. I think he knows I can do this stuff (and I know I can too), while my prof is doing his subtle best to make me feel like an idiot, and question my ability to become a doctor! I soo wish I could say this to my boss but if I do manage to move onto Orgo II I still have to deal with this prof so I of course won’t lol.
(oops…didn’t mean to rant there lol).
Thanks again Vera!
–Jessica, UCCS

Is anybody else struggling the way you are? You could form a study group, work problems together, and explain them to each other. Even if you partner with someone who’s doing WORSE than you are and explain EVERYTHING to them, you’ll benefit enormously.
If you need to see reaction mechanisms, try the site for my textbook, McMurry’s 6th edition It has animations, online quizzes, hints, and practice problems that have you do several of the same kind of reaction in a row. This might be a way to spot your trouble spots and reinforce just the things you’re weak in.
Hang in there, and keep on twising your head around until you find a way that works.

Don’t let this class stress you out, I know it is easier said than done. When looking at some huge WTF molecule look for a functional group first, do not let the size freak you out. The functional groups is usually were all the action is at and go from there. You must memorize all reactions which it seems that you did, but you also have to understand what is going on. Yes, you have to know Diels-Alder but also how and why it is happening. Speed is essential if your exams are really long so you have to be fast as well. Have you invested in a dry erase board? and do this reactions until you puke…do not get nervous in the exams and be confident in your abilities. This class is not that hard if you take your time and understand electron movement. Good luck and keep us posted.

have you tried talking to yourself? or working the synth backwards?

seriously, staring at Ochem synth problems is hard. When I memorized/learned the reactions, I tried to verbalize them by what they did - e.g. add -OH to alkene - or 6 ways to make an alcohol, or breaking open a ring - and I’d test that way too - not just what do you get if you add A to B ? but “what will add an -OH”, “what will make an amide”, “what will add a -X to an alkene” ? I call this learning the REACTION and not just the REACTANTS.

for me the A reacts with B to form ??? problems were not the toughest ones. the A —> C name the reactant type were hard. So I’d verbalize the difference - C is A with an -OH at position 2 – what can add -OH to make 2nd alcohol ?

It is all just a giant puzzle (not a puzzlement)


maybe you will find these helpful too
Ochem Songs - can’t get along with out a rousing course of Gringard the Beautiful can we? Or my fav, Glory, Glory It’s Wolff-Kischner

More directly related to studying:
Ochem Study aids sites:
Ochem flashcards:
Reaction quizzes:
Synthesis help:
SN1, SN1, E1, E2:
Lots of helpful stuff:
Exam review lecture notes, practice exams:
Links to tutorials of various aspects of Ochem:

I knew this was the place to come for help lol. Thanks for all the great links Lisa. I’ll have to wait for next week probably to actually check them out between a physics exam tomorrow, and a huge organic extra credit assignment (only worth 25 pts tho but every lil bit helps ) due Monday.
The McMurry text site looks helpful too compared to Carey’s text site, samenewme. As far as a study group I’d love to set one up but unfortunately I don’t own a car and am at school in class or at work already 8-5 everyday. If I don’t catch a 5:30 bus I have to walk a mile and a half with a backpack full of books in the dark lol.
Efex - your suggestion of how to study is exactly the stuff that’s not clicking. I understand how the electrons move around fine for indiviual mechanisms, but it’s a matter of figuring out what things will add what under what conditions that I’m constantly mixing up. Thankfully this next quiz and the final will cover Diels-Alders which is something I do a lot of for my work study. (I’m trying to find ones that don’t take days to fully react and can potentially be used for lab classes.)I’m definitely going to try harder to consciously ask myself and write down these types of things lol.
Thanks again guys :slight_smile:
–Jessica, UCCS

Good luck on your exams!

Ok, I just went to the chemistry songs site… this is absolutely unbelievably hilarious!!!
Thanks for posting…
As far as organic 1 goes…
I suggest making alkane, alkene, alkyne, benzene reaction “wheels”… This seems to help a bit.
Also try doing lots of problems…
I find working reactions out on a chalkboard or a wipe board is also a good idea…
I will be studying for finals here in the next couple of weeks… so I’m right there with you (Org II).
Good luck! You’ll get it… with determination like you have, you’ll figure it out…
Incidentally… I have talked to several chem majors and grad students… and they’ve told me that they really didn’t “get” chemistry until the middle of organic II… I can see, to an extent, what they mean… but I’m not switching my major… LOL
Take care!

Hi Skaterbabe,
When I was taking organic, I used to take a blank page of paper, draw a functional group in the center (say an alkene), and then draw arrows pointing radially out, with different reagents above each arrow, and pictures of the products of each reaction after the arrows. This worked really well for me, since I’m a lot better at remembering diagrams than say, Excel spreadsheets, which tend to remind me of bank statements. You might want to try something like that if you haven’t already.
I hope the class is getting a little better!

Hey all Thanks again for all of the suggestions. After talking with my boss we think that it’s mostly a confidence issue. I know what’s going on, I understand the material,I do well on the homework and additional problems, but I’m just getting flustered when I do things and make stupid, costly mistakes, like dropping a carbon somewhere lol. I like both the “wheel” and spreadsheet ideas, and I spent a lot of time copying things down from Lisa’s links for when I start reviewing for the final. I really liked the Townson and UIC websites. The funny thing is that one of those links is from my own professor but for whatever reason he didn’t include that particular summary on the site this year. I now only need to get myself up 3.8% points between the extra credit, the last 2 homeworks, the quiz next Thurs, the remaining daily in class quiz points, and the final so I “should” (fingers crossed) make it.
(Oh and I think I did well on my physics exam last week but won’t find out til after the break - our prof is really slow at grading lol).
Thanks again, and Happy Thanksgiving everyone!
–Jessica, UCCS

Well today was our last quiz for Orgo I. He turned it into a group quiz so I finally aced one hehe. Thankfully the group that I normally sit with includes the “brain” of the class (the one with 102% lol), but the quiz wouldn’t have been that awful if we’d been doing it on our own anyway. Diels-Alders are definitely my friend lol. Now I just have to do decent on the final but I think I’ll be fine. I don’t think I’ve ever been soo proud of a C in a class lol. Hopefully I’ll be able to kick butt in orgo II tho :slight_smile:
Thanks again everyone!
–Jessica, UCCS

Which text are you guys using? We are using the Morrison & Boyd book, which is really good at explaining everything in excruciating detail.
Of course the interesting thing about all the sciences is that the things that PhD’s were working on in the most heavily guarded labs 100 years ago are now summarized in one paragraph halfway through chapter four…I suppose the tradeoff for that is that when it’s all said and done, we’ll be able to use MRI’s and lithotriptors instead of leeches.
(A diol is basically an alcohol with two hydroxyl groups instead of the one an alcohol is carrying around…not tough at all!)