NEC's O-Chem Survival Guide


TABLE OF CONTENTS


Welcome to O-chem!

My Brain Ain't Big Enough!

Where to Turn?

T-45 Minutes and Counting...

Chem 2311, 3, 5, 7, 9?

Helpful (?) Hints

Where Others Fear to Tread

A Final Note



Welcome To O-Chem!!!

You've read about it, you've heard about it, now it's your chance to actually live, eat, sleep and breathe O-chem!!! First of all, always keep the following in mind: many have traveled the treacherous trails of O-chem before you and survived, and you can too. That is basically what this Guide is all about. So, as they say in The Hitchhiker's Guide to the Galaxy, DON'T PANIC, and read on as you begin your O-chem adventure.

My Brain Ain't Big Enough!

The average length of the typical organic chemistry textbook (the kind used in any year-long course in O-chem) is about 1,230 pages. Ours "weighs in" at about 1,100. IF we worried about cramming all of this precious and undoubtedly vital information into our brains, that would mean covering about 50 or so pages each week. The good news is: quality, not quantity!!! We won't get through the entire book, although we will still cover a substantial amount -- this is the nature of the beast. My philosophy is: learn the fundamentals (the tip of the iceberg) well; the remaining bulk of organic chemistry can be learned with remarkable ease if you can just learn these basics well.

Learning the basics, on the other hand, is not so easy! It requires incredible fortitude to resist the temptation to memorize everything. Contrary to very popular belief, O-chem is not about memorization. Granted, there are some aspects (like nomenclature) that you cannot avoid memorizing, and granted a rare few are able to memorize and retain, without confusion, the vast sea of information presented in organic. The majority of us are lucky in that O-chem is not a vast sea of unrelated information, but instead is a network of highly predictable patterns relating physical properties to the reactivity of compounds. To learn how to recognize these patterns and therefore be able to predict the reactivity and physical properties of a compound you have never seen before is the ultimate learning experience of organic. It is learning how to think. It will make your life much easier, and thus the take-home message here is: yes, _______________ (your name here), your brain is big enough!

SO. Memorization is not the answer -- learning the fundamentals and therefore learning to recognize the interrelatedness of all organic reactions is. This interrelatedness, the pattern found in organic chemistry, is what we call electron movement. Organic chemists focus on the movement of electrons from one compound to another in a reaction to form a new product. The movement of electrons is known as the "mechanism" of a reaction, and is the aspect of organic chemistry that makes it predictable. We will slowly, but surely, be introducing you to the concept of "pushing electrons" throughout fall semester. If mechanisms / electron movement / resonance structures / Lewis structures are throwing you for a loop, all is not lost! There is a very useful workbook called "Pushing Electrons" (by Dan Weeks) that drills you through the concepts associated with electron movement. If you need some additional help and are motivated to do a little extra work on your own, you can purchase it at the bookstore and WORK THROUGH it early and often!

Where to Turn?

Now that you are fully aware that memorization will only bring you great grief and sorrow, and that mechanisms are bound to be your salvation, let me clue you in on some other details that will help you on your journey.

1) Materials. There are old tests floating around! Yes, it's true. In fact, they are available to you on this very website. I will post last year's quizzes and/or exams about a week or two prior to us studying that material. Word of warning! We don't always cover the exact same stuff, nor at the same pace. So last year's quiz/exam is not always a completely accurate representation of what this year's quiz or exam will look like. Also note that knowing the material covered on last year's test will in no way guarantee you a good grade on this year's exam. Furthermore, having last year's quiz/exam may encourage memorization and cramming, two vile curse words in the world of Chem 2301-2! SO -- examine them, if you wish, as a helpful indicator as to how you're doing, and as a reflection of what type of problems you may expect to see. But the similarities end there. I will also post lots of other stuff on here besides old exams -- summaries, additional explanatory info, extra problems, etc. Keep checking this website regularly!

Your old tests: I generally return graded exams in class. Look through your graded papers!!! They are your friends, even if you got more wrong than you got right. It is very helpful to study your old exam, find out where you went astray, and LEARN FROM YOUR MISTAKES! The keys for all exams, quizzes, and homework (not from the book) will be posted outside my office.

2) Academic Assistance Center. Many have gone before you -- and survived! Now they are willing and able to help you survive. The AAC oversees the "chemistry drop-in" tutoring in the Chem Lounge; I'll announce those details in class. The AAC also has many good ideas about how to succeed in your classes. Check out the AAC web site or drop by anytime.

3) Studying in groups. Nothing helps you survive a trial better than to commiserate with a friend who's in the same boat. You are not alone. To that end, I strongly encourage working together groups in lecture so that you can work/study together both inside and outside of class (but sorry, not on tests!) Of course, you're not obligated to study with "your" group and your group only, and I would strongly encourage you to seek out your colleagues and work together, quiz each other, and talk O-chem with them (just don't let anyone else hear you! They'll think you're a science nerd!).

4) The Web. A wonderful opportunity exists to set up study groups without the hassle of finding a time/place to meet, etc.: just study, discuss, ask questions via the campus computer network! The O-Chem Cafe has been set up as a discussion group on this WebVista page and I invite you to use it as an "O-chem bulletin board". If you have a question, an insight, a comment -- anything related to O-chem, post it at the O-Chem Cafe. The goal is to get just about everyone in o-chem regularly reading and contributing to the discussion, so that an efficient electronic exchange of ideas and helpful information can take place. I will also use the discussion board quite regularly to communicate to the class as a whole (hints, sermons, pep talks, practice problems, reminders...). So please avail yourself of this resource! It is very convenient and accessible anytime!

5) Help Sessions. A help session is an opportunity to get together with your colleagues and discuss O-chem in the presence of the evil ogre who is causing you so much grief -- yours truly! Absolutely anything is fair game at these sessions -- work problems, ask questions, discuss the meaning of life, etc. All are welcome to come and shoot the organic bull...

The Smorgasbord. As you can see, there are lots of resources out there to help you through O-Chem. But the main thing to remember is to take advantage of all of these resources, and not rely on only one or two. For example, coming to lecture, but rarely reading the book or doing the problems, will reap nothing good. The most sucessful students make use of their lecture notes, the text, the miscellaneous readings file, talking with friends, and talking to me (!) to help them understand the ins and outs of o-chem.


T-45 Minutes and Counting...

The exam is a mere 45 minutes away. You had a calc test yesterday and a paper is due this afternoon. You've been up all night cramming for this O-chem exam. YOU'RE DOOMED!

Well, you're certainly not doomed, but you're not going to do as well on the exam as you could. Organic does not take cramming well. Your brain turns to mush (trust me -- I've seen it happen, and it's not pretty...). Therefore, a BIG key to success in O-chem is staying caught up!!! Get a routine, chain yourself to your desk, study O-chem in the shower, do whatever you have to do, but DON'T get behind. Granted, there are going to be days where your other classes are calling, yelling, screaming your name! This is the nature of college life. Go ahead. Work on Physics for a couple of days. Write your paper for Ethics. But DON'T, DON'T, DON'T, blow off your O-chem. Work on your O-chem EVERY DAY, even when time is tight. Be selective, be wise. When time is at a premium, don't intently review the material we covered two weeks ago. But at least go through your lecture notes, and skim the text material we will be covering in the next lecture. Try working a problem or two. But limber up the O-chem part of your brain daily -- a little regular exercise prevents serious injury later on. (A word of warning here -- I help you stay caught up in the fall semester by giving frequent quizzes. In the spring term the number of quizzes may drop significantly, so that you're pretty much on your own. This is life!)


Chem 2311, 3, 5, 7, 9?

You're probably going to find this hard to believe, but the things you learn in lab are actually related to what you are learning in lecture. So another way to reinforce what you are studying in lecture is to think about it as you work in lab, do your lab write-ups, etc. And vice-versa! Just think -- it's almost like doing two classes for the price of one?!?!?

Helpful(?) Hints

There is no simple list of "ways to success" in o-chem. I've already mentioned all kinds of resources to help you, and the cardinal rule (see the big block letters above). But when it comes right down to it, YOU are the only one who can get you through o-chem. My (admittedly idealistic) advice:

Review your notes after every class. Stay caught up with the reading, and do the homework problems early and often. In other words,

DON'T GET BEHIND!!!!!


(it bears repeating).

Test yourself BEFORE the test. Far too often I hear pleas of "I know this stuff, but then I get to the test and just don't have a clue!!!" Guess what? The material on the test is the same stuff we talk about in lecture, and that is in the text. SO, ask yourself how do you know that you "know this stuff"??? Unless you put yourself in the test-taking situation and test yourself, then you do NOT know whether or not you really know this stuff. It is an unfortunate fact of life that we assess your knowledge of the material by exams. It would be great (?) to spend 30 minutes or so talking o-chem with each of you individually, so that you could convince me that you know this stuff, but it doesn't work that way. SO, two suggestions.

  1. At some point, work homework problems randomly. Pick several problems from each chapter (or each section), and write each one on an individual piece of paper. Put them all in a paper bag, shake it up, and take one out and work it. Period. Make this the same as an exam situation: no Study Guide, no text, no nothing. If you "know" this stuff, you will be able to solve the problem. But once a problem is taken out of context (as on an exam), it is MUCH more difficult to solve, and it requires that you develop a thinking approach to the problem, not just a rote response, recalled because you remember, for example, that this problem is from the pKa section of Chapter 4. If you find that you don't know this stuff, crack the book and work hard to develop this thinking approach by working more problems, and/or come talk to me.

  2. Several days before the exam, find a quiet place where you will not be disturbed, set the timer for 60 minutes, and take the old exam. In other words, put yourself into a situation that is as similar to that of taking the exam as you can. This way you prepare yourself for the "pressure cooker" of taking the exam. When the real exam comes, you'll have already gone through the experience and thus will be more relaxed and able to do your best (in theory!) If you get the completed old exam to me at least two days before the exam, I'll correct it for you, so you can find out where you need to concentrate.




Where Others Fear to Tread

As stated at the beginning of this Guide, many before you have survived the dreaded O-Chem. Some former students (all of whom survived!) have graciously offered their advice to you who now begin the journey, and I reproduce it in this Guide, unabridged:


Tips for surviving O-Chem

First off ask for help when you get lost. Go to a classmate, someone who has passed O-Chem or what I would suggest talk to the teacher. Do not think that you can just get it on your own by struggling through it.  You might be able to get somewhere but more than likely you will just get more frustrated. I’m not saying don’t try you need to put effort in to understanding it but O-Chem has a lot of concepts that are new and take some work to get used to them.

Second stay caught up with everything, do not become an O-Chem chipmunk. What I mean is don’t horde it all like a chipmunk does with his nuts. Because what will happen is you’ll go to class with your brain full and you will not understand it because you didn’t digest the things from last class. It will just all build up and then you’ll just want to give up because you’ll be so lost.  So how do you avoid this? You do your work but not all at once, take it in chunks. If you try and take it all in one sitting, you will get frustrated. You need to take O-Chem in small chunks. Try and make it a goal to spend half an hour a day on O-Chem. Along with doing the reading do the problems. In fact I would say working through problems is more important because they are a good way to tell you if you understand it or not. Also don’t use the study guide as a crutch. You should only look at the study guide once you think you have the right answer.  That means if you don’t know how to do a problem you ask someone instead of looking at the answer in the study guide. Doing problems in groups is useful too because you can help each other out.

Third, review old tests. It can be painful to go though old tests and look at what mistakes you made, but would you rather learn from your mistakes or would you rather get that some concept wrong again on the next test. O-Chem just builds on itself like math -- if you don’t understand addition you’re not going to understand multiplications.

- Meredith Lorig (Class of 2008)


WARNING: The sentences following this disclaimer may actually help you survive Organic Chemistry. Taking Organic Chemistry may lead to anxiety attacks, sleep apnea, constipation…(My first advice for you is to RELAX! :) )

You hear the phrase used all the time…everyone is in the same boat. So let’s close our eyes and imagine that Organic Chemistry is a ship sailing across the sea. (Just bear with me.)

1. Oh, No! Your ship is lost at sea… (aka The lectures make no sense and you are totally lost).

Treat your textbook and notes like a map, they have all the directions that you will need to make it to the final destination. However, youhave to be able to interpret, understand, and follow the maps for them to help. COME TO CLASS PREPARED (even if you only have 5 mins. to skim the chapter). READ THE TEXTBOOK and YOUR NOTES (it may help to re-copy your notes after class) GET INTO a ROUTINE (make organic chemistry a habit that you do every day.)

2. Oh, No! You fell overboard… (aka You get behind or you just bombed an O-chem test.)

If you find yourself struggling, confused, frustrated, or BEHIND…. DO SOMETHING ABOUT IT!  You have to be willing to tread a little water and look for help if you plan on keeping your head above the water. Don’t panic. If you take the time to look around you will realize that you are not the only one treading water (drowning). It is easier to tread water in groups than alone. STUDY IN GROUPS AND QUIZ EACH OTHER. Remember there are people all around you reaching out a hand to help. ASK FOR HELP WHEN YOU NEED IT!!!!

3. Oh, No! There is a big storm and you want to turn the boat around…(aka you stink at O-chem and want to drop out.)

The end is closer than you think. Don’t give up. The professor will not give up on you!!! Learn from your mistakes. If you don’t understand something don’t just skip it and tell yourself you will figure it out later. You need to struggle through the problems to the very end and then USE THE ANSWER BOOK WITH EXTREME CAUTION. Learn from your mistakes and keep at it! “When you get to the end of your rope, tie a knot and hang on.” ~Franklin D. Roosevelt

Just remember that everyone is in the same boat (or in the water trying not to drown)…you are not alone. Good Luck and :) Happy Sailing!

An O-chem survivor,

– Julie Fox (Class of 2008)


Here's my advice:
  1. Don't get behind on the reading. Everything you learn builds on stuff you already know. Learning everything the night before the test doesn't work.
  2. If you have questions, ask. Ask different people the same question. If you don't understand how one person explains the concept, someone else might make sense.
  3. The profs are there to help. They're usually pretty good about it, too. Use them.
  4. Labs always look intimidating. The instructors and TAs are really good about helping. Don't sweat it, just be sure to read the procedure beforehand.

- Rachel Gartner

O-chem can be simple for some and difficult for others. I was one that found it more difficult than any other chemistry course I'd taken. But, however difficult I thought it was, I did survive! Here's what I have to suggest, and you'll probably hear the same things over and over through the semester. Oh! I almost forgot, and I know you'll hear this one a lot: HAVE FUN!

--Amanda Appel


As for advice to future ochemers tell them to:
--Tami Ganske



Thinking about O-Chem kind of got me in a real sentimental mood so I wrote a poem to tell you all about it. While you are reading this, keep in mind two things. There is always help (Nancy, TA's, Beaker, Tutors, and even that strange guy down the hall) and everyone is in it together. With that small piece of advice, you can now read this beautiful piece of chemical literature entitled FTIRGCNMRHPLCTLCILUVMYMOM.

Electrophile Nucleophile NMR GC I love thin layer chromatography Beilstein Diels-Alder Carpenter and her crew They are the chemists that are out to get you You got a pair of goggles and a lab notebook Now get your CRC and go swim in a brook (??) Though you may think this is one big game After this year you'll never be the same Just one word of caution, just one final thing This here is Ege, I'll see you in the spring.
- Kris Roth



I Survived O-Chem, and You Can Too
O.K. I'm a pretty smart kid (all of us here at UMM and in o-chem are pretty smart kids). I've always just been able to balance school and sports and fun social gatherings, and I've even gotten super grades without feeling like I've made huge sacrifices. Then I took o-chem. It's different. I knew this before the class began and so was rightfully scared (as you should be too); but I handled my fear in a rather self-destructive way.

First, I figured if I was to be successful in o-chem I'd have to devote all my precious time locked in a room sweating out solutions to monster problems. I didn't want to do that (as any college student driven by immediate gratification). As a result of my attitude, a second problem arose, I got behind. Then I became a bit overwhelmed. Then I got more behind and more overwhelmed. Pretty soon I had so much work to do I just didn't know where to start. So I didn't. Thus I lived in a downward spiral.

Fortunately, I not only ended this downward spiral, but somehow turned it in the opposite direction, eventually leading upward. I'm proud to say I had a relatively strong finish and that qualifies me to give you a few pointers.

First, don't get behind. Oh? You've heard that already? Fine, but you have to alter your thinking too, if you're like me. Staying caught up doesn't mean every second devoted to o-chem. You can employ 20 minutes a day to be caught up. This is unlike history, where you can read the chapters the night before the exam; and unlike english, where 20 minutes gets you next to nowhere. Plus, o-chem itself is a social activity. There's a very strange bond between o-chem students.

Now, I'd like to be arrogant enough to think you all will follow my advice and never encounter my second problem of landing in the o-chem hole, but inevitably, a few of you will. I've got some stuff to say to you. First, being overwhelmed and scared is fine, except fear is an enemy. Fortunately, action cures fear. Do something, anything to chisel away at the mound in front of you and simply believe you can climb out of the hole. That's key. Don't give up on yourself and Nancy won't give up on you either. She is a super resource. Oh, and don't fall asleep during class....

- Kari Simmelink



Tip #1: When a new reaction is introduced in the text, there is usually a mechanism drawn for the reaction. Take the time to fully understand the mechanism before you continue reading the chapter. Oftentimes the subsequent reactions in the chapter are very similar to the preceding reactions. Thus, don't continue to build confusion on top of confusion, understand the reaction before you continue reading. I found it very useful to read the chapter with a pencil in hand, doing the "arrow pushing" for the mechanism myself, justifying to myself why that mechanism is the "most correct mechanism" (i.e., has the most stable intermediates). After fully understanding the mechanism of the reactions, I would make note cards to help myself memorize the reactions. This is done for the sake of the limited time available to take exams.

Tip #2: I know Nancy has told you this and you all laugh and think she's insane but, she is right. Learn to work synthesis problems backwards, (i.e., product ---> reactants) it will help you immensely in the future. By the way, I would be willing to entertain conversations with any of you regarding Nancy's sanity. As I know, many of you are beginning to seriously wonder about someone who would choose Organic Chemistry for a career. Seriously, learning to work synthesis problems backwards will not simply be a good idea. Rather, it will become a necessity when you start working larger synthesis problems. Developing good habits early on in the course can make Organic Chemistry much easier and yes, dare I say, even enjoyable. Believe me, I was the last person in the world who would ever think they would enjoy Organic Chemistry.


- Jerry Beyer



A Final Note

I hope you survive and (God forbid!) maybe even enjoy your journey through O-chem. Hard as it may be to see, there is an awful lot of what you will learn in O-chem all around you, and I don't just mean organic chemistry, either.

If you find that you are just having a horrendous time with this course, think you are flunking,* or are thinking about dropping -- hey, for whatever reason, even if you want to talk about the Cubs (!) -- come see me in Sci 2085. I am here to help you survive O-chem. Please, don't hesitate to come by and give me a chance to do what I can.





© 1997 University of Minnesota, Morris

The views and opinions expressed in this page are strictly those of NEC. The contents of this page have not been reviewed or approved by the University of Minnesota. Last Modified: Monday, August 10, 2009
Page URL: http://www.morris.umn.edu/~carpenne/nec_homepage/survival.shtml

The views and opinions expressed in this page are strictly those of the page author. The contents of this page have not been reviewed or approved by the University of Minnesota.

The views and opinions expressed in this page are strictly those of the page author. The contents of this page have not been reviewed or approved by the University of Minnesota.