
How to Get an A- in Organic Chemistry - danso
http://www.nytimes.com/2013/11/03/education/edlife/how-to-get-an-a-in-organic-chemistry.html?pagewanted=all
======
alex-g
The author suggests that we need "future doctors who are less Spock and more
Kirk". I ask: "What about Bones?" In addition to actually being a doctor,
McCoy has conscience, dedication, loyalty to his patients, and technical
skill.

~~~
JasonFruit
Of course, that's "actually being a doctor" in the sense of being a fictional
character who was written as a doctor. You can ask too much of a facile
comparison.

------
mililani
I took orgo as an undergrad from a brutal professor. His name is Marcus Tius,
and he is legendary at UH Manoa for being hard. He got his Ph.D. in organic
chemistry at Harvard from EJ Corey. Most people on here probably don't know
who EJ Corey is, but he's widely considered to be the greatest chemist alive.
And Corey's lab is insanely intense. A few of his grad students committed
suicide in recent years from the pressure. Supposedly, I don't know if this is
urban legend, but EJ Corey told several others that Tius was his best student
ever at the time.

Anyways, I just wanted to share a few of my orgo stories. Our first exam mean
scores were in the 20%'s. Only 10 of us got above 70%. There is NO curve in
his class. He talked about this after the first exam, and he said, "Many of
you are asking me if there's a curve. I wouldn't hesitate to call 90% and
above an A." The first test was so brutal, that after he called the 15 minute
left mark, a whole sea of "HOly shit! WTF?!" spread throughout the lecture
hall. It was shortly after that, one of the students was escorted out by a
grad student proctor because he peed his pants. I was already light headed
from the intensity of the exam, but seeing a guy literally pee in his pants
almost made me pass out.

In retrospect, orgo isn't that bad. If I had taken it the previous year with
another professor who was using the McMurry textbook, I would have even said
it was pretty easy. But, no. I was stuck with Tius, and I was stuck with an
entry level graduate textbook on organic chemistry--this part is no joke.
However, in retrospect, I also realized Tius wasn't bad either. I realized
that if I just worked on his assigned problem sets and studied those for the
exams, I would have done fine. The exam mostly consisted of the problem set.
So, he was very fair. However, all of the urban legend stories made me so
scared, I was doing all the problems in the chapter which often took 50-60 hrs
a week to complete.

For anyone thinking about taking orgo, it's really not that bad. However, like
any other course, the professor and books can make it incredibly hard. Just be
wary of that.

BTW, I did get an A in both orgo courses. I majored in math and chemistry, and
I have to say, that class with Tius was by FAR the hardest shit I ever had to
go through. And that includes a general chemistry course with another brutally
hard chem professor in which I stood up three nights in a row to study for the
third exam because I was so behind. I got an A in that class too.

~~~
revelation
It seems necessary to make exams that hard when they do not determine the
grade anyway (the OP got an A- with a B on the final exam).

Let me expand on how it works in a German university. There are no curves, the
concept is completely foreign here. Your grade is 100% determined by a final
exam. You do exercises only to get approval for writing the final exam in the
first place.

~~~
jcampbell1
It sounds like your exams are more like Microsoft Certifications rather than
US university exams. At top US universities, it is common to include questions
that only one person in 100, or zero in 100 will get right. I took plenty of
Math exams with 10 questions, where getting 5 would earn an A, and 8 is how
many grad students would get right, and the 10th question was a joke, like
Fermat's Last Theorem. The exams were not to demonstrate you are certified in
a subject, but rather to show your ability and limits.

Not grading on a curve is a horrible idea. It means the exam must be limited
to material that is taught, rather than limiting it to known knowledge in the
universe. German University sounds like a big ass certification program, not a
real university.

~~~
EliRivers
_Not grading on a curve is a horrible idea._

Maybe I misunderstand what this curve grading is all about, but doesn't
grading on a curve mean the grade is not a measure of how good one is, but how
one compares to other people who happened to be taking the exam at the same
time? So you don't have to be any good to get a top grade - just better than
other people taking the exam at the same time? And likewise, you could be the
world's tenth greatest living chemist, but if the other nine people taking the
exam are the world's top nine, you'll fail.

And _not_ doing this is "a horrible idea"?

~~~
jcampbell1
This is a complex issue. Harvard grades everyone on a curve, and basically
never gives lower than a B. They use "A+" as a system to identify the truly
exceptional people.

My point is that a professor should be able to write 20 questions that are
relevant and interesting, and just look at the distribution of results to
assign grades. I think that makes sense, rather than turning university exams
into certification style exams.

My answer to why, it is a horrible idea to not grade on a curve requires and
anecdote:

I took an impossibly hard math course with about 15 students where the average
grade was a 2, I got a 4, one guy got a 6, and another guy got an 8. The
professor gave me an A, but in reality, I was 4 orders of magnitude dumber
than the best student. Professors have discretion. The main reason I tell this
story, is that the guys that got a 6/10 and and 8/10 have both gone on to have
an 8-figure net-worth (fuck-you money). One through finance, and another
through a startup. It has been awesome to see the people that I know are
insanely smart become insanely wealthy.

The important part of this anecdote is that the professors that wrote the exam
wrote two questions that one of smartest humans on earth could not answer. How
fucked up would the world be if the professor had only written the 4 questions
we all got it right? Asking impossible questions creates greatness. Grading on
a curve enables professors to find truly exceptional people.

~~~
EliRivers
What you've written here doesn't make much sense; possibly because the reason
you wrote it wasn't to support your argument but to tell us you went to school
with some people who became very rich.

"How fucked up would the world be if the professor had only written the 4
questions we all got it right?"

This just doesn't make sense. What are you trying to say? Did you mean to ask
"What happens if there were only four questions and we all got it right?"

"My point is that a professor should be able to write 20 questions that are
relevant and interesting, and just look at the distribution of results to
assign grades."

Fine. My point is that this means you're being marked on the basis of how well
you did compared to everyone else who took the exam, which means it's not a
measure of how good you are; it's a measure of how good you are compared to
the others taking the exam. If the purpose of taking the exam is to
demonstrate you know the material, grading on a curve subverts and corrupts
that purpose. Any exam in which your mark depends on how well other people do
in the exam is a nonsense; your mark should only depend on how well you do in
the exam. If the professor knows the exam is horrifically difficult and thinks
that to score twenty percent is amazing, you should get a good mark for
reaching twenty percent, even if everyone else scores fifty percent.

~~~
monkeyspaw
Grading on a curve helps normalize the resulting letter grades based on how
well everyone else in the class understand the material, as it was presented.
You are correct in this.

I believe it acts as a check to make sure that the class is well taught, and
the questions of an appropriate difficulty level.

If every student receives an F for a 40% correct (and they all only get 40%
correct), a curve normalizes that. Students who understand the material as it
was presented and tested better than others receive a higher grade.

Makes good sense to me. The problems arise in the Harvard situation, where
nobody is curved down. If you down curve inflated scores downward, then a
curve only serves to inflate grades and is less useful.

~~~
vubuntu
"If every student receives an F for a 40% correct (and they all only get 40%
correct), a curve normalizes that. Students who understand the material as it
was presented and tested better than others receive a higher grade."

If every one in the class was lazy to study/prepare for the exam and every one
ended up getting less than 40% correct, then they all deserve to get F.
Normalizing with a curve means, it's possible that someone who got only 39% in
that exam in a class full of lazy folks who all scored much less than him, can
earn a A or A+ ! Compare this to similar class/exam taken by different set of
students (all brilliant) at a different time or place, who all worked hard and
scored above 80% but still some of them could get B or C's due to curve
grading. Wouldn't it be unfair to the 80% scorer who got a C whereas some one
who scored a 39% on the same subject got A+ due to circumstances (time and
peers he took the exam with) !! How is that fair at all?

~~~
jsharpe
This is an invented objection. In reality, in classes of sufficient size,
there is always a subset of students who work hard (or are extra smart, or
whatever), a subset who is average, and a subset who slacks, or just doesn't
understand the material well. The objection that there might be a mass class
conspiracy to all score 40%, or that everyone in the class will be lazy, just
doesn't make sense.

~~~
011011100
Who says it's a conspiracy? It's more a matter of culture. I have seen it
happen: there's a trend in the class where the homework grades, on average,
are high, but the exam grades are low, even though the material is mostly the
same. This happens at reputable schools and at "low tier" schools.

------
ezl
I was an organic chemistry TA for a professor who was notorious for having the
hardest organic chemistry class at our school, but it was also widely
considered that surviving his course meant that you truly understood the
subject matter.

He was unapologetic about the subject matter being difficult and believed that
teachers who didn't teach it hard and try to really force undergrads to
understand it were cheating themselves.

He was especially adamant about it because many undergrads taking organic are
trying to go to medical school and didn't like the idea of letting lazy or
stupid people become doctors on his watch.

When we were grading tests, he would laugh as he marked errors and delivered
low grades. "Hexavalent carbon? WRONG. Saving lives... Saving lives..."

------
pvnick
Orgo is a double edged sword. The flow of electron density that dictates
bonding patterns between the machinery of life is fascinating and graspable
intuitively. The problem comes when you get to those useless professors who
prefer not the theoretical but the practical applications of industrial
synthesis, who enjoy shoving heaps of reactions with various reagent
combinations down their students' throats. As a result it becomes impossible
to think mechanistically as I believe a good organic chemist should, and
instead studying is reduced to carrying around stacks of note cards and
memorizing different chemicals, solvents, and temperatures. _That 's_ hell,
because it's stupid and a waste of time.

~~~
jasonpbecker
This is true. Some of the reason that American students in particular have a
hard time in organic chemistry is the insistence of teaching intro orgo by
functional group rather than reaction mechanism. In the UK, it's far more
common to organize a course around mechanisms (which is how most graduate and
advanced orgo is taught).

The functional group approach exposes you early and often to seemingly non-
sensical (or at least challenging) exceptions that don't seem to follow any
pattern, all of which makes perfect sense when you learn them grouped with
other situations where the same mechanism applies.

------
danso
FWIW, the OP is a professional science writer...that is, she's written books
about scientific topics and has also produced for scientific-themed shows like
NOVA. Her undergrad was in American Studies.

I'm pointing this out to give her more credit for making the career change (at
42) to become a doctor. It'd be different if she were an engineer who became a
science journalist and then later decided to become a doctor...This is
assuming that if you didn't do something like o-chem as an undergrad (many
engineers do o-chem or an equivalent hard science topic to graduate), doing it
at 42 is quite the brave shift.

~~~
woud420
I think one of the quotes in the article resumes it perfectly : "Sometimes, if
a student has really good math skills, they can slide through physics, but you
can’t do that in orgo". If they would concentrate a little bit more on physics
and math, they'd get to realize the "exceptions" based on cold, acid, etc...
can be explained instead of just memorized.

~~~
dnautics
Although I advocate for chemists to know more physics, what you are saying is
not true. There are exceptions that can be rationalized based on general
principles of physics, detailed understanding of physics is not necessary. The
relationship between physics and math is not the same as the relationship
between chemistry and physics. Much of mathematics (especially college-level
calculus, versus say, college theoretical algebra) were explicitly created
with physics in mind. So with an encyclopedic knowledge of calculus
transformations, a semi-educated guess at the appropriate transformation is
possible. You're even better off if you understand dimensional analysis.

This is not true for chemistry. Even chemists disagree vehemently on why, for
example alkanes are staggered in the lowest energy conformation. Is it because
the electrical charges in the hydrogen electron orbital clouds have a weak
repulsive effect? Or is it because the hydrogen electron density can partially
donate into the sigma antibonding orbital and stabilize the conformation at
the expense of a little bit of bond stability?

------
anusinha
There are two points regarding the relevance of organic chemistry to future
doctors that the article could expand on further.

1\. Organic chemistry is often the first class that a prospective future
doctor takes that requires you to develop proper study habits. One can get
away with most other introductory level courses in the sciences by cramming
during the day or two before the exam. Organic chemistry is different--it
requires structured and daily studying. This is an essential skill for anyone
planning to go to medical school.

2\. Organic chemistry teaches you to thing and reason about objects in three-
dimensional space. Stereochemistry (roughly: if something is right handed or
left handed) is an essential idea in organic chemistry. Being able to think
about objects in 3D space is a very useful ability (and necessary) for a
future doctor.

------
krakensden
> Medical schools are tweaking admission protocols, looking beyond an A in
> orgo for future doctors who are less Spock and more Kirk. > I asked two
> medical school deans — Dr. Robert Witzburg at Boston University and Dr. Lee
> Goldman at Columbia University — about admission philosophies. Both are
> proponents of holistic review, the newish idea that medical schools look
> beyond grades and test scores to evaluate the whole applicant

You should always read this as code for "to reduce the number of Asian
students admitted".

~~~
abat
Not always. In the past holistic review was to keep Jews out of the Ivy
League. The minority being targeted will probably be different 50 years from
now.

That said, I do agree that soft skills are probably valuable for doctors.

------
base698
My data structures course in which I made a B- was much harder than Organic I
and II which I made A+'s by never getting any question wrong on any exam. I
never figured out why that was and have wondered why I saw one harder than the
other. Maybe if labs were not so boring or monotonous Id of been a chemist or
maybe programming is much harder.

~~~
berntb
I can't say you're objectively wrong, but my experience differs dramatically.

I am a really lousy cook. I am not handy; I'm fairly certain my relatives
laugh at me behind my back. And I did high school chemistry lots of years
earlier. In short, a background which promise pain when studying organic
chemistry.

I was so stressed in the lab, that when a small fire started between me and
the exit (a student used a poor way of evaporating she'd learned in a previous
course), I just thought " _Ah, the fire extinguisher is by the exit with the
other students, someone else can stop the fire, I 'm too busy._". Luckily,
someone did. (This fire was a minor scandal; could have really damaged the
accident statistics.)

That said, the organic chemistry and lab work was incredibly fun and giving.
It really surprised me that I loved the subject.

You needed protective covering, built interesting stuff, used vacuum to
evaporate, boiled stuff in oil baths to get much higher than water
temperature. You could read the "things I won't work with" blog (
[http://pipeline.corante.com/archives/things_i_wont_work_with...](http://pipeline.corante.com/archives/things_i_wont_work_with/)
) and shudder at the FOOF formula.

Much more fun than biochemistry lab. Much more fun than sitting on a chair in
front of a screen.

If I hadn't been sick (unknown food allergies and bacteria infection in a
tooth, both of which made me tired), I might be a chemist today. I got through
the course but had to quit later.

Edit: I might add -- my present back problems from sitting in front of a
screen for decades might force me to an unpleasant/dangerous operation in ten
years.

Edit 2: Half the reason I liked Org Chem was probably that the subject had to
do with reality, it was such fun after just studying/working with totally
abstract concepts my whole life.

~~~
lyagusha
Completely agree. Created an account just to say that the lab work (for orgo
1) was the single most fun, fulfilling class I took in college. It's probably
why I like to cook very much.

------
sampo
I took Introduction to Organic Chemistry part 1 on Coursera. (And passed it.)

It was the worst executed Coursera class I have taken. The lectures contained
only the bare bones of the theory and almost no examples, and there was lots
of difficult homework (of the sort the NYT article describes). Even if they
would want us to have no theoretical foundation, and just generalize from
examples (like the NYT article suggests), they should have told us that that
is the M.O. of the course, and then actually give us a large number of
examples to stare at.

Of course intro level organic chemistry is no secret knowledge, and there are
good textbooks, but what's the point of an online course (or real university
course lectures), if just reading a proper textbook would be more beneficial.

Any subject can be transformed into a difficult course by teaching too little
theory, and then giving too advanced homework.

------
tcbawo
I took a night class in organic chemistry at 30, considering a career change
that I never pursued. It was fantastically challenging, which was what I
needed at the time (I wasn't getting enough from my job). After the
experience, I completely understand why this class serves as a proxy for
medical school admissibility. For someone who almost never studied, I suddenly
found myself doing an hour or two of homework each night. Going back to school
and getting the 'A' from a top 10 university was one of my proudest academic
achievements. I highly recommend taking a few classes out of your comfort zone
to recharge your batteries.

------
im3w1l
> “It seems a lot like diagnosis,” said Logan McCarty, Harvard’s director of
> physical sciences education, who taught the second semester. >“That
> cognitive skill — inductive generalization from specific cases to something
> you’ve never seen before — that’s something you learn in orgo.”

I wonder why people can get away with saying stuff like this without evidence.
I'd be inclined to think that the diagnosis boosting from orgo is minor at
best and the time used would be far better spent actually learning to make
diagnoses.

~~~
jamesash
It is similar in that both require applying concepts to solve very specialized
situations. This neurologist agrees with McCarty and can tell you why:
[http://bit.ly/16WUkba](http://bit.ly/16WUkba)

~~~
im3w1l
His argument "Sounds like Organic Chemistry doesn’t it?" is exactly what I am
criticising. Sounding similar, doesn't mean there will be strong synergy
effects.

I give that there could be _some_ synergy effects, but I highly doubt there
are strong enough that it's better to study orgo rather than what is actually
being applied.

------
Mister_Snuggles
> But the rules have many, many exceptions, which students find maddening. The
> same molecule will behave differently in acid or base, in dark or sunlight,
> in heat or cold, or if you sprinkle magic orgo dust on it and turn around
> three times. You can’t memorize all the possible answers — you have to rely
> on intuition, generalizing from specific examples. This skill, far more than
> the details of every reaction, may actually be useful for medicine.

Ignoring the specifics about Organic Chemistry, this skill, relying on
intuition and generalizing from specific examples, is the skill of Pattern
Recognition.

Regardless of the subject, you can't memorize all of the possible permutations
and combinations, but you can start to get a feel for the patterns and begin
to recognize them. Then when you encounter something new, you can recognize
the pattern, or enough of the pattern to have a place to start.

Think about things you do on a day-to-day basis and how you react to a new
situation. You just signed up for a new service and you get your first bill in
the mail - you've never seen this bill, but it fits the pattern of every other
service you use and you already know how to pay it. Now apply that same
concept to something more complex than paying a bill.

I'd love to see a course like this in every field of study since pattern
recognition is a skill that everyone has but so few seem to do really well.

------
ssully
Pretty neat article!

My girlfriend is a bio major and we have talked for hours about the pain and
crushing defeat that org-chem can bring. I always likened it to calculus for
me, since math has always been my weak point, but I never had a calculus exam
that made me feel the way org-chem seems to make some students feel.

Also major respect to the author. Making that kind of career change in your
40's has to be difficult. I wish her the best of luck.

------
suchire
Orgo is, in many ways, like learning a foreign language, in that the
memorization early on is supposed to support and later be superseded by
understanding the "grammar" of how things fit together. I think the way orgo
is often taught, or perceived, as being _just_ about memorization is what can
make it soul-crushing and not all that effective.

The introductory orgo classes I took early in college were heavy on reaction
mechanisms, molecular orbital theory, and intuition and light on memorizing
bucket-loads of reactions, and it ended up giving me and my classmates a much
better grasp of the material than students from other schools. Many of us
ended up breezing through our university's graduate courses in organic
chemistry while graduate students from other universities struggled painfully
through the same courses. I suspect that it's part of the reason it was the
top organic chemistry program in the world.

------
dnautics
I took grad-level orgo. It was a firehouse of knowledge. One of my professors
was Phil Baran, who just got the MacArthur award (for his work in orgo)...
Literally got hit by a car the day before the final, (went to the ER and
everything, but no broken bones); came hobbling in to the exam. First time I
ever failed a class in my life, but I came back the next year, and passed. I'm
so glad I did it; though I don't actively use organic chemistry in my day-to-
day I can go to conferences with organic chemistry and understand 90% of what
they are saying.

------
cschmidt
Our orgo textbook must have been 4 inches thick. I can still remember in the
first lecture, when the professor said, "your homework is to do all the
problems in the book." All of them. Luckily I had an easy semester otherwise,
so I sat in the library, and did untold pages of problems.

That said, p-chem (physical chemistry) was a lot harder ;-).

~~~
trentlott
I'm in a PhD program for chemistry, learned calculus when I was 25, and I
thought PChem was pretty intuitive.

~~~
cschmidt
I suppose it depends on the professors you have. I had an excellent orgo
professor, and a rather bad p-chem professor.

He was the hardest grader of any professor I ever had. He gave (partial)
negative points for an incorrect answer on tests. I had friends who ended up
with negative scores on their tests. The class average score was in the 30%
range. I had one friend who managed to get every single question wrong on a 20
question true false section, which to this day still amazes me. Luckily it was
on a curve, or he would have failed us all.

Eventually, I gave up trying to understand p-chem, and concentrated on just
learning his very strange test style. That turned out to be a fantastic
decision for my grade. I got the high score in the class on the last test and
the final, which got my grade up from a B- to an A-. The downside was I never
really learned p-chem ;-).

------
discardorama
Hard-ass instructors aren't confined to orgo.

I had a professor in calculus. His tests were multiple-choice, with 1.0 for
correct and -0.25 for every wrong answer. So even if you answered _nothing_,
you would get a 0.

The average in his exams used to be -1.5 or so. You made an "A" if you got >
2.5 out of 15.0

~~~
keypusher
If the average was -1.5, why not just answer nothing?

~~~
discardorama
That is the point! People were just too proud to leave the test blank; they
thought they knew the material. But the wily old fox would trick them, and
very few saw through this tricks.

------
refurb
This just goes to show you that personal interest goes a long way for these
difficult subjects. I always found org chem fascinating and eventually got my
PhD in it. I always found it very intuitive and not that challenging.

However stuff like advanced mathematics is completely beyong my comprehension.

------
marincounty
1\. We need more medical schools. 2\. Free medical schools completely funded
by the government. 3\. We need to weed out the students who want to make money
off their patients, or future Dr. Ego's. 4\. Reading this reminded me of
college, and it seemed like everyone was premed, and for all the wrong reasons
--mainly Ego. Oh, how they wanted to be called Dr.. 5\. If you really want to
become a doctor--for the right reasons--take your premed courses at a low
income community college. You will ace the course. 6\. Once you become a
Doctor, don't use it as a stepping stool. Want to become wealthy--marry a rich
kid. Want money and an Ego stroke--go into finance, or learn Ruby on Rails,
but stay out of medicine. Want a baby in the middle of your career, and never
plan on returning to medicine after your husband makes his wade--fine, but
stay out of medical school--you just wasted a coveted spot.

good luck--grade grubbers!

By the way, I always felt the difference between A students and B students was
a lot of ass kissing--at many colleges.

------
mtdewcmu
I liked o-chem, and I took 3 semesters of it, even though I was only minoring
in chemistry. Its reputation as super-hard might have been motivation for me.
Synthesis is a little like programming.

~~~
dnautics
It really is!

The mental part of planning a synthesis is a lot like programming. The
differences are: parts (i.e. reactions) are less interchangeable, and when you
actually make the stuff, you get diminishing returns, "recompile" is not as
trivial a task.

Synthetic biology is a lot closer, since you can copy DNA at will, and while
editing is not as simple as spinning up an instance of vi, "recompile" is a
whole heck of a lot easier.

~~~
mtdewcmu
I didn't take the organic chem lab course, because I had a bad time in lab I.
The o-chem lab might have been better, since it was supposed to be more
qualitative and less quantitative, so maybe it would have been less
susceptible to shaky titration hands... but I didn't want to chance it. The
analogy to programming only goes so far, but the differences were enjoyable to
me, since I had plenty of exposure to real programming.

