
TABLE OF CONTENTS 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. 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. 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! 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... 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!) 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. 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. 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)
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....
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. 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.
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!!!
My Brain Ain't Big Enough!
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!
Where to Turn?
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!
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).
Where Others Fear to Tread
- Meredith Lorig (Class of 2008)
Here's my advice:
- 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.
- Kris RothElectrophile 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.
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.
- Kari Simmelink
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.
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.
- Jerry Beyer
A Final Note
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.