Seven Workout Areas in Organic Chemistry

Most points on Organic Chemistry exams are lost in weak areas that are highly preventable, i.e. areas requiring a constant "workout." I've been keeping a mental tally for over ten years on where errors are routinely manifest, how they're made, and how such errors can be avoided. You can read this article in less than five minutes, apply what is discussed, and increase the score on your next exam by a percentage directly proportional to the amount of energy you invest in strengthening certain areas.

7 Workout Areas in Organic Chemistry

1. Confusing oxidations with reductions, using oxidizing agents such as PCC to reduce carboxylic acids, and using LAH to oxidize alcohols. This happens more frequently than anyone might imagine. There are two ways to avoid this trap. First, understand the oxidation states of carbon, and know how to calculate them. Second, make compound cards for all "letter reagents" such as PCC or LAH, being certain to indicate on the backs of such cards the structure and reactivity of the reagent. Also, understand that an oxidation is a loss of electrons to an oxidizing agent, and that a reduction is the gain of electrons from a reducing agent.

2. Losing skills in drawing Lewis structures. This becomes highly influential on exam scores beginning around week 15 of Organic Chemistry when electrophilic aromatic substitution is introduced as a topic. The reactions are easily memorized, however the mechanisms are not, and require the ability to draw highly relevant Lewis structures for every functional group.

3. Losing skills in resonance and drawing resonance structures. Arguments in Organic Chemistry are based in sterics and/or electronics, and resonance falls within the electronic category. Aromatic chemistry, electrophilic or nucleophilic, is understood when resonance is understood. Likewise, understanding resonance is necessary for learning and applying carbonyl chemistry.

4. Losing skills in understanding acid-base equilibria, what's a strong acid and what's a weak acid. Just as 95% of Organic Chemistry is explained by a nucleophile going after an electrophile, it's also explained by a Lewis base going after a Lewis acid, hence 95% of Organic Chemistry is Lewis acid-base chemistry. This was the reason for learning the concepts in week 2.

5. Confusion about what's the nucleophile and what's electophile in the reaction. Of paramount importance, the most nucleophilic center must be identified, as so must be the most electrophilic center. It's better to master these subjects early. After week 20, many molecules will have multiple nucleophilic and electrophilic centers, and a weakness in identifying such centers will lead to total confusion.

6. Understanding retrosynthetic analysis. This is the area wherein students lose the most points. Most of us are auditory-sequential learners who excel at performing tasks in a forward-thinking linear sequence. It just so happens that the synthesis of complex organic compounds are not amenable to this type of thinking. It's crucial to learn to think backwards as early as possible, to confront the discomfort and frustration head on (we're talking about your ticket to professional school here!), to struggle and then conquer. Avoidance of retrosynthetic analysis will not make it go away, rather tackling it head on will lead you to mastery.

7. Remaining comfortable. The first time I used this phrase was on a friend in graduate school who couldn't understand why he was unable to surmount a problem. Somehow, I realized in 1988 that the key to success in life was in becoming comfortable with being uncomfortable. Please think about this statement for a few days, and you'll understand the wisdom that some people never learn in a lifetime. When you're struggling and uncomfortable, you're really learning!

Why Students Fail Organic Chemistry

Regardless of where Organic Chemistry is taught, regardless of the genius and/or talent of the professor, and regardless of any variable that can be conceived, there is a percentage of students who will fail. The average midterm grade in Organic Chemistry ranges between 25-50%, hovering around 38% for classes having professors who challenge their students. Typically the first midterm includes concepts of acid-base chemistry, pKa, valence bond theory, Lewis structures, resonance, hybridization, alkane nomenclature, Newman projections and radical chain reactions. As the material is introduced, students study in a manner identical to that which sufficed them since high school. Some periodically review their notes, and convince themselves they know the material. It's not until 4 days prior to the first midterm that they begin working the problems.

The first midterm is incredibly easy, although there are ways to make it far more challenging than you might imagine. At least two professors I know do this. If a student obtains an A or B grade on the first midterm, a certain false sense of security sets in. All of a sudden the course their upperclassmen said was the "killer" is simple... deceptively simple. The deceptively simple feeling is part of what leads students to fail Organic Chemistry.

The next midterm focuses upon application of the principles learned in the first four weeks, covering cyclohexane conformations, principles of conformational analysis, haloalkanes, stereochemistry, basicity vs. nucleophilicity, and finally SN1 and SN2 reactions. The principles learned for the first exam are considered long departed and irrelevant to the second exam. This couldn't be further from the truth. All of nucleophilic substitution is Lewis acid-base chemistry with a particular emphasis upon solvent effects. This midterm has a different feel to it, however the same behavior is exercised in preparation for it, with most students working the problems as late as 4 days prior to the exam. This is a major factor leading students to fail the course.

Suddenly the students with A and B-grades have scored B and C-grades. There's a feeling of shock when that exam comes back with the results. Each and every student feels as though s/he knew the material, however the grade doesn't lie. Suddenly, there's a commitment to "try harder" on the next exam. Material includes E1 and E2 reactions, conformational analysis, NMR and IR spectroscopy, and fundamental electrophilic addition reactions introducing the rearranging carbocations. Albeit the student may focus more for this exam, the study habits still have not changed. Come time for the next midterm, C and D-grades become manifest.

Material for the final exam covers electrophilic additions to alkenes in great detail, builds further upon reaction mechanisms, introduces fundamental carbonyl compounds, oxidation and reduction chemistry, utilizes organometallics such as Grignard reagents and alkyllithiums, and finally stresses synthetic Organic Chemistry, heavily focusing on retrosynthetic analysis. Each student is determined to get an A on the final to have a shot at a B or better. Still students fail, and immense frustration ensues.

Why do students fail Organic Chemistry?

The highest contributing factor leading students to fail is sporadic studying, focusing on the work immediately prior to the exam. In essence, it's choosing not to master time management. Furthermore, many students will invest equal time in reading the textbook as in working the problems. It's very common for students to spend far more time on the easier problems than on the challenging problems. The next highest contributing factor leading students to fail Organic Chemistry is clinging to the "skill" of memorization for dear life. Students who fail know it's better to learn to rationalize the problems and use logic, however the memorization approach is very comfortable, just like a comfortable glove.

This "comfortable glove syndrome" is what leads students to fail Organic Chemistry. It happens every semester, in every city, and in every school. Students fail Organic Chemistry because they cling to memorization for dear life. If Organic Chemistry is a "killer," then memorization is the gun firing the bullets. Repeat this to yourself three times.

You don't have to fail Organic Chemistry. If you have any faith in my words, or in the words of your professors, you'll realize we're all saying the same thing to you. Memorization is worthless and will cost you your grade. It will lead you to fail the subject. Building your logical and deductive reasoning skills will lead to you ace it.

It becomes rather simple. Memorize and fail Organic Chemistry, rationalize and ace Organic Chemistry. Unfortunately many students don't come to this realization until the course is over. Why? One single three syllable word...

de-ni-al [dih-nay-uhl] noun:

    refusal to believe a doctrine, theory or the like;
    disbelief in the existence or reality of a thing;
    the refusal to recognize or acknowledge.

Denial is the most dangerous of all defense mechanisms because it leads us deeper and deeper into deficit, sometimes becoming so deep that it feels like a great chasm from which there is no escape.

This isn't my typical upbeat and positive writing style. I'm not sugar coating anything in this article because I want you to get the point without any possibility for bargaining or denial. As a matter of fact, when confronted with the realization that memorization will not work in Organic Chemistry, the student will proceed through 5 stages:

    Denial;
    Anger;
    Bargaining;
    Depression; and
    Acceptance

These stages, popularly known by the acronym DABDA, were observed by Dr. Elisabeth Kübler-Ross when working with people experiencing catastrophic loss.

Organic Chemistry is unlike any science course you will ever take. It's the only course that brings chemistry majors to me in tears. Learn to excel - you can do it! Build your logical and deductive reasoning abilities. Study 20 hours per week. Reading the book doesn't count as study. The only thing counting as study is the diligent working and reworking of problems. When working the problems, ask yourself, "What would happen if I changed this variable?" Become inquisitive, get creative.

When my students ask me to give them the key for success, I always respond with the same line I've been using for the past 25 years. "Become comfortable with being uncomfortable." Dependence upon memorization is a behavior that you've built for 15+ years. A deeply seated behavior like that, especially one that has brought rewards, will not be countered easily. You must become the master of your own behavioral modification.

When extremely focused, it takes 90 days to modify a persistent behavior. I'm challenging you right now to transition from memorization to deductive reasoning.

This challenge will make you feel like the guy free climbing the mountain. This is where an exceptional tutor is of most use. Contrary to popular belief, exceptional Organic Chemistry tutors are not for digging you out of a hole. They do their best work when coaching or mentoring you as a Master Trainer would mentor a budding Olympic athlete. Exceptional Organic Chemistry tutors facilitate the behavioral modification process though guided learning.

Aspire, Achieve, Master, Succeed! Failure runs away from this attitude. Do yourself a favor, build some attitude, the right one. Ace that Organic Chemistry class!

10 Secrets to Master Your Organic Chemistry Course

Organic chemistry is probably the most challenging of science courses that you are going to experience in your college career. The sheer volume of information which you have to study is overwhelming, and the failure rate is unusually high. Yet there is no way around this path if you are pursuing a career in the profession of health or science.

Although there are no miraculous solutions to acing this course without the required hard work and dedication, there are a number steps you can take, and methods you can implement to insure that you don't fall behind in organic chemistry. This will make it easier for you to stay on top of the material and ultimately on top of the academic curve.

1- Reading Your Textbook Prior to Lecture
Read your textbook right before lecture. You simply can't afford to arrive to class unprepared. If you hear the principles and mechanisms for the first time during class, you can be overcome as you frantically attempt to break down the material and grasp the basic key points.

Reading through the chapter ahead of time, regardless of whether you don't fully grasp everything, It ensures that you'll be able to have some knowledge of the material mentioned in lecture. After you are exposed to the information for the second time in lecture, your primary focus is shifted to comprehending the concepts which you found originally challenging in your readings.

2- Take Notes During Lecture
No matter if you are recording the lecture, or have a set of printed PowerPoint slides, you still ought to take notes during the session. This can help you stay focused, stop you from tuning out the professor, and may help you identify the little stresses placed on individual ideas or mechanisms. These will likely wind up being the very points tested in your approaching examination

3- Read Your Textbook Once More After Lecture
Now that you have a much better comprehension of the material, it is best to read the book again to make sure that you are comfortable with each topic discussed and mechanism tackled

4- Practice, Practice, Practice
Organic chemistry is not a course that can be soaked up through simple memorization. You should practice the principles, check your understanding of the ideas, and consistently go through each one of the mechanisms. The more familiar you are with each factor, the less the chance that you may be caught off-guard on the exam

5- Do More Than the Assigned Homework Problems
If you stick with just the 5 or 10 given homework problems, you are cutting yourself short. The additional problems located in your book are intended to test the same concepts, with a somewhat unique twist every time. When you practice these added problems you'll be better equipped to resolve unforeseen challenges on your upcoming exam. These kinds of additional questions may even be the very questions that may turn up in your test

6- Do Not Memorize
The worst thing you can do to mess up your organic chemistry capabilities is to just memorize reactions. When you memorize an exact reaction, you are only equipped to answer questions presented in the form memorized, consequently you will be caught off guard when the starting compounds or reagents are somewhat, or completely different from your flashcards. However, if you review the concepts, focusing on how the molecules behave, and the reason why the electrons attack, you will be capable of completing any related mechanism, regardless of how the reacting substances are presented

7- Study Groups
Any time you study by yourself you are restricted by your individual sources of know-how, notes, and study material. Whenever you study with a group you will be capable of assisting the other person with difficult ideas, and process mechanism challenges as partners. If you are weak in a particular matter, your study group will be able to address your concerns. And if you are secure with a subject matter, you will probably still learn it far better whenever you are required to apply it in easy terms to describe to a member of your study group who has trouble understanding this concept

8- Peer Tutoring
A lot of universities have a learning center with peer tutors to assist you with your organic chemistry course. Even though they are students on their own, these tutors have taken, and effectively completed organic chemistry, and will therefore be able to help you with the basic concepts and mechanisms

9- Office Hours
If your professor or TA has office hours, consider this a very skilled, very free tutoring session. Your teacher and TA are quite familiarized, not merely with organic chemistry, but also with the concepts and problem forms that will show up on your examination. They'll be able to assist you to fully grasp the facts by using problems similar to what you will later be tested on

10- Private tutoring
Though the above mentioned tips are extremely effective guidelines not to be dismissed, many students still find themselves having so many doubts with insufficient resources. Study groups are tied to the experience of the students concerned, and peer tutoring or office hour sessions are typically rather crowded.