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Anyboy taking/taken organic chem? Come on in...

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Loki

Count of Concision
For anybody who has taken or is currently taking organic chem 1 (first semester, obviously), I just wanted some feedback on the exam shown below; I was wondering what your take on it would be, difficulty-wise: average, semi-difficult, hard etc. I'm just trying to get a feel as to where everybody is in the course and how other professors test as compared to mine. When assessing the test (which was my first exam in orgo, given last week), keep in mind that we were given only 50 minutes to complete this exam. So what do you think? Comparable to exams you've had? More difficult? Less difficult?


The subjects we covered prior to this exam were nomenclature/structure (i.e., hybridization states, molecular shapes/planarity, bonding orbital shapes/directions etc.), acidity/basicity, halogenation, stereochemistry (enantiomers, diastereomers etc.) and stereochemical reactions (racemic mixtures, net inversion etc.), including optical activity, conformational isomers (Newman projection diagrams etc.), SN1 and SN2 reactions, and solvent effects (we only lightly touched upon solvolysis prior to the exam; we mostly covered which types of solvents would favor SN1/2 and what the products would be etc.). We did not specifically cover the rxn's of alcohols (except how you'd convert them into alkyl halides etc., as per question 9, and also how they become protonated to form oxonium ions which are good leaving groups for SN1/2 etc.). Hyperconjugation (question 14b) was mentioned for a grand total of 35 seconds in class, with no supplemental readings assigned in the book, as it's a topic to be covered in depth much later in the course; an industrious student would have read it anyway since it was mentioned, but who ever thinks a professor is going to throw an entire question in on something that was discussed for literally 35 seconds, considering the amount of other material covered).

No templates were provided on the answer sheet for any question besides the first, which appeared exactly as it does on the question sheet; question 3 was the only "quick" question, and the only multiple choice question, on the exam-- the rest were long-answer and needed to be written out in their entirety on the answer sheet).


I'm just very curious as to what others think...


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So what do you guys think? Fair? Comparable to exams you've taken (in orgo 1, first exam)? I'm just honestly curious, because we were VERY pissed off that there were so many long-answer questions. I managed a very good grade ("A" level) on this exam, but could have done much better if given an extra 10-20 minutes. His exams are notoriously difficult, but even students of his from previous semesters said that this exam was much harder than even his usual fare-- mostly because his other exams, of the sort he has posted online from previous years (and he has dozens of his old exams online), all contained at least 3-5 "easy" or "quick" questions, such as question 3 in this exam or quickly-answered questions such as "is the equilibrium greater than 1, less than 1 or approximately equal to 1 for the following rxn's?" (these would be acid/base equilibria reactions, which are quickly determined based upon relative acidities). In light of this, the time was really a factor here. In addition, he usually throws in a simple energy diagram question (either of the transition state for, say, bromination/chlorination, or of the anti, eclipsed, and gauche conformations of a certain conformer via Newman projection), which can likewise be done very rapidly.


Any feedback (or commiseration :p) would be appreciated. :)


EDIT: Oh, and props to my anonymous forum friend for helping me with hosting these pics, without which this glorious (yes, glorious I said :p) topic would not be possible. :)
 

Pfucata

Member
I agree that time pressure can be an issue, but it doesn't look much different from tests I've taken. That is, most of the questions are fair questions -- stuff you know how to do or stuff professors always harp on during lecture. Some of the unusual questions that take a long time to answer feel like they're the examples that the prof gives in lecture and that you can try to reproduce verbatim (like 10 through 13)
 

Loki

Count of Concision
Pfucata:

Are you taking orgo right now? :) How are you finding it? I actually like it more than regular chem, in terms of enjoying the material. To give you an idea, the class average on this exam was a 36 (130 students); I got a 72 (A = 70+; only 15 students got above a 70), but felt that with another 10-20 minutes, I could have had an 85+.


Question 10 has to do with whether or not the bond to the chiral center on the butane is broken or not (that is, whether the reaction proceeds via SN1 with the ethanol, or SN2 with the sodium ethoxide, which preserves the specific rotation to the same degree, but in opposite direction due to inversion).

For question 11, the general rule (as I'm sure you know) is that increasing the solvent polarity DECREASES the rate of reaction via SN2; this is a special case, however, because the transition state is MORE stabilized than the reactants by increased solvent polarity (due to the partially developed charges on the transition state as compared to the neutral substrate and nucleophile), thus lowering the activation energy and increasing the rate. So it's counterintuitive in that sense.

Question 12 is just a simple bromination transition state sketch (transition state reached late due to the high activation energy, and has much radical character); question 13 was from a lab we did.


As you can see, it's not really that it's difficult so much as the time was an issue. For instance, how quickly can you do questions 1 and 2? For myself, for the first question, I had to draw out the carbon skeleton formally, THEN do a Fischer Projection diagram, THEN translate that into the Newman projection. Due to the complexity of the molecule, this took a bit of time. Ditto for question 2 (in terms of mentally picturing the enantiomers/diastereomers etc.); question 4 is the same deal: the structure had to be drawn out and then the various chlorination products obtained; these then had to be combined into the various fractions, where necessary. Question 9 also took some time.


I was just curious to see what other people thought; I did well, but I studied the wrong way for this test-- you have to just do dozens of problems...and more problems...and more problems (particularly the ones from his past exams) until it becomes so second nature that you can do them without thinking, really. All I did to study for this was to reread the chapters and lecture notes for understanding. I didn't really practice doing any problems; needless to say, this will change for the next exam. :p
 

bionic77

Member
Been awhile since I took Orgo, but the exam seems to be about on par difficulty wise. Hell, some of the questions seem very similar. I think we had 2 hours for our exams though and I don't remember how long it was in comparison to yours. Too long ago, should have kept tapes...... :D
 

w0o

Member
I remember organic chem..took 2 semesters of it. My profs were hardasses with long and difficult exams. In fact one even even warned us that we would most likely not be able to finish all the questions in the time alloted. Half of the questions were of the relatively easy type...short answer/multiple choice/matching. The other half were damn hard un-bullshitable questions which only the brightest students could manage to answer correctly.
Thank god the course was graded on the curve. I managed to get a 7/9 with a 55% average :D
 

bionic77

Member
w0o said:
I remember organic chem..took 2 semesters of it. My profs were hardasses with long and difficult exams. In fact one even even warned us that we would most likely not be able to finish all the questions in the time alloted. Half of the questions were of the relatively easy type...short answer/multiple choice/matching. The other half were damn hard un-bullshitable questions which only the brightest students could manage to answer correctly.
Thank god the course was graded on the curve. I managed to get a 7/9 with a 55% average :D

I remember the mean was ridiculously low when I took Orgo. I didn't think the class was that hard actually, but it was one of the most boring classes I took in college.
 
I don't know, that seems to be a bit rough just considering the time factor. I took orgo four years ago as a freshman and my memory are clouded by booze and girls, but I'm fairly sure that our exams had at most 7 or 8 long-answer questions to be completed in a 50-minute period. The exam averages ranged from 27 to 55 if I remember correctly.

On a side note I took the class specifically because they told freshman that they shouldn't even if they received a 5 on the Chem AP test. But I said fuck it...went to class... and fell on my face. I was truly grateful for the 'pity C' I was given by my Prof.
 

Loki

Count of Concision
Richard Cranium said:
Hmm, looks more difficult than some of my tests, and about the same as some others (I've taken ochem 3 times!). Is the test curved?

Yeah, it's curved, but it's a bogus curve. Usually (for non-science courses) in my college, the mean is curved up to a C-, so that sets the distribution. For this course, he curved it, but the average (which was a 36) was still failing. A "D" ran from 40-50; a "C" from 50-60; "B" from 60-70, and "A" was a 70+. To give you an idea, 53 kids got 50 or better (C), while about 80 got < 50, with 55 kids getting < 40, and hence failing for this exam. He's really the only science professor that curves his tests at all, because they're notoriously difficult, both for the material as well as the time constraint (this was more of the latter than the former; for some of his old exams, it's the opposite-- more difficult questions but less time pressure). So yeah, he curved it, but if you happened to get the average or even slightly higher (36-39), you still got an "F" for this exam. Weird...


Btw, I finally got around to sending you a PM at Opa-Ages; check it out when you get the chance. Between this class, physics, psych and genetics, I've been very busy. : /
 

Loki

Count of Concision
reggieandTFE said:
I don't know, that seems to be a bit rough just considering the time factor. I took orgo four years ago as a freshman and my memory are clouded by booze and girls, but I'm fairly sure that our exams had at most 7 or 8 long-answer questions to be completed in a 50-minute period. The exam averages ranged from 27 to 55 if I remember correctly.

Yeah, his old exams (the first exams, at least) all had around 7-9 "long answer" questions, with the others being either multiple choice, qualitative comparison questions as noted earlier, or energy diagrams/transition state sketches etc.). This test has 15 long answer questions; with the exception of the bromination transition state long-answer Q, there really aren't any that you can just fly through. I lost some credit on the fractional distillation Q because I realized that I was never going to get through the entire exam if I didn't speed up a bit; as a result, I made a silly oversight and forgot to separate 2 diastereomers into 2 separate fractions. : / The time pressure really got to me (and my classmates, from what I hear). Like I said, though, if I prepare differently for the next exam, even that shouldn't bother me as much. I barely worked any practice problems in preparation for this exam-- I relied on my understanding of the concepts (which is not always sufficient when you need to do these things so rapidly). Still, I'm pleased with my performance.
 

Loki

Count of Concision
Btw, Reggie and Bionic, why did the two of you take orgo? :) Bionic, you're in law school, and Reggie, aren't you doing a master's in either economics or political science iirc? Seems odd that the two of you would have taken it, unless it was on a bet. :D
 

Cloudy

Banned
I was gonna take Chem as a science elective my first year of college but I ended up dropping it 3 class periods in. Now I remember why >_<
 

bionic77

Member
Loki said:
Btw, Reggie and Bionic, why did the two of you take orgo? :) Bionic, you're in law school, and Reggie, aren't you doing a master's in either economics or political science iirc? Seems odd that the two of you would have taken it, unless it was on a bet. :D

For the same reason I took Discrete math, to get the minor degree. I liked Biology and I needed Orgo to get the minor. I really didn't think the class was that bad to tell you the truth, just a ton of work (at least that is how I remember it).
 

Loki

Count of Concision
Cloudy said:
I was gonna take Chem as a science elective my first year of college but I ended up dropping it 3 class periods in. Now I remember why >_<

Heh, it's not as bad as it looks; it's just that each semester really builds on the previous one (less so for organic outside of certain concepts; it's pretty much an entirely different type of course from general chem, more concept-based than chem 2's more mathematical focus in terms of the questions you're asked). I happen to really like chemistry (both general chem and organic); if it weren't for these damn exams, I'd have no stress at all lol, because I really enjoy the material, and consequently grasp it more quickly than some other students who can't stand to look at the stuff. :p To give you an idea of how much I enjoy chemistry (and how big of a geek I am), I'm actually looking forward to reading through my general chem text again over winter break. Yes, I'm that[/] sad of a person. ;) Well that, and it's good review for when I eventually take the MCAT. :p
 

Loki

Count of Concision
bionic77 said:
For the same reason I took Discrete math, to get the minor degree. I liked Biology and I needed Orgo to get the minor. I really didn't think the class was that bad to tell you the truth, just a ton of work (at least that is how I remember it).

Hah, that'll teach you for trying to get a bio minor! :D So you're a fan of biology, eh? Cool; did you have to take one semester or two of orgo? The bio majors at my school have to take the full year (and one year of general chem and biochem, too), but I'm not sure about the minor requirements.

And yeah, the course isn't that difficult, per se, it just takes a lot of work (which I haven't been giving it, despite my good performance on this exam-- that's the story of my life :p); most of the kids in the class are giving just this course between 20-30 hours/week of studying; I really only do the assigned readings once and read over my lecture notes, maybe 8 hours/week, if that (with the exception of the 6 days before the exam, where I put in about 50 hours of studying, which basically consisted of rereading the text and NOT working problems, which is what I should have been doing). I have to step it up a bit, though, because I don't wanna get screwed for finals and have to review everything from the beginning of the semester again. :p Blast this accursed board for keeping me from doing that! :D


What was your major? I know that most universities don't offer a "law" major, though some do. I hear philosophy is a big major for people applying to law school (understandably).


EDIT:

I'd just write down "True" for all and hope for the best.

That's why you have a small pecker. ;) :p
 

bionic77

Member
Loki said:
What was your major? I know that most universities don't offer a "law" major, though some do. I hear philosophy is a big major for people applying to law school (understandably).

Economics. I minored in Math and Biology.
 

Loki

Count of Concision
bionic77 said:
I had impressive nerd powers in my youth. They diminish with age though.

I'm not exactly a spring chicken myself, you know. ;) That's why it's all about the videotapes. Videotapes = periodic reabsorption. :D Oh yeah, reading a book once in a while helps also. :p
 

draven

Member
Taking orgo I now: already took our first exam, and am slated to take the second this week. I only made it halfway through your exam and started to feel guilty as hell for looking at a gaming forum reading about someone else's orgo test rather than study for my own.

From what I saw, yeah, looks pretty difficult, especially since I'm just covering that stuff myself. Then again, I haven't taken my second test yet. It seems kinda long, especially for an hour.
 

Loki

Count of Concision
From what I saw, yeah, looks pretty difficult, especially since I'm just covering that stuff myself. Then again, I haven't taken my second test yet. It seems kinda long, especially for an hour.

50 minutes, not an hour. ;) That was our first exam (given on Oct. 14), not our second (our second exam is slated for Nov. 18). You didn't cover most of that material for your first exam? What subjects did you cover for your first test, then?


Maybe your semester starts/ends later than ours? Ours is from August 27 til about Dec. 13 or so, and then 8-10 days for finals. Also, are you taking regular organic chem or organic chem for health and nutrition majors? (many schools offer this as a separate course from regular orgo, and it's eaiser and slower-paced)
 

Tsubaki

Member
Mmmm O-chem. At my worst, I got an 11/100. But the mean was a 37 so I really didn't flunk that bad...

Anyway, your test is about par as far as Ochem tests go. Ochem is one of those classes that is a nightmare if you don't get it, but fun when it clicks. I really liked it.
 

Loki

Count of Concision
Tsubaki said:
Mmmm O-chem. At my worst, I got an 11/100. But the mean was a 37 so I really didn't flunk that bad...

Anyway, your test is about par as far as Ochem tests go. Ochem is one of those classes that is a nightmare if you don't get it, but fun when it clicks. I really liked it.

Yeah, it really is very interesting; some of my friends in the class-- even some who did very poorly on the exam-- enjoy the material a great deal. How'd you end up doing after that 11? Hopefully you passed the course. :)
 
Just kinda breezing through the exam, it looks fair. If you'd ask me to do any of it, I wouldn't be able to help ya there. :)

I remember the worst O-chem problem I had was a large molecule, and the only direction was "just let it happen."

Learn O-chem for the class, for the MCAT, and then you don't really need it after that. NONE of the biochem in med school has required you to remember it, aside from a few key concepts (cis/trans formation, numbering systems, and a few things about resonance) but you will NEVER have to recall specific reactions.

Don't know if that helps or not.
 

Loki

Count of Concision
IAmtheFMan said:
I remember the worst O-chem problem I had was a large molecule, and the only direction was "just let it happen."

:lol

That honestly made me laugh out loud. :p

<student looks at exam>

"Professor, I'm about to shit my pants!"

"Just let it happen..." :lol

Learn O-chem for the class, for the MCAT, and then you don't really need it after that. NONE of the biochem in med school has required you to remember it, aside from a few key concepts (cis/trans formation, numbering systems, and a few things about resonance) but you will NEVER have to recall specific reactions.

Yeah, I've heard that from a few people in med school; the exception, obviously, is if you're doing an MD/PhD with a concentration on biochem/pharmacology, I would imagine. :p

This is also why the MCAT has less orgo nowadays on the biological sciences section and more genetics and microbio-- to more reflect the realities of which topics are en vogue in med schools currently. Or so I've heard.


Studyin right now for an exam in the morning over basically the same things yours was.... :(

I'm sure you'll do fine. Best of luck. :) Hopefully you won't have 15 long-answer questions in 50 minutes. :p

Oh yeah, if you can get a hold of your exam paper after the test, it'd be cool if you could post it in here like I did, so I can get a better feel for others' tests. :)
 
The test looks pretty fair. If the material is mentioned in the reading/syllabus/etc, then it should be fair game. A lot of the questions these questions could be done from rote memory... some are pretty common in practice tests etc. I think you just need to practice more (and WRITE LESS) so these questions become second nature.
 

Loki

Count of Concision
I don't have to do anything, really-- I did very well on the test, considering. :D I was just curious as to what others thought about it. But yeah, for the next exam, I'm gonna do more practice problems and less rereading of the chapters/lecture notes, because that'd help me to be able to do the questions faster, which is the only reason I didn't do better. Oh, and the resonance structure/hyperconjugation stuff wasn't in the readings; in fact, it's supposed to be covered in our Nov. 11 lecture, according to my lecture outline. It was just mentioned briefly for about 30 seconds. What a weirdo my professor is. :p


Are you in orgo now, eggplant? Or have you taken it recently? I'm just curious as to how long it would take you (or anyone) to do the first question in particular. Believe me-- the test is fair enough, but to do it in under 50 minutes puts you in a pinch. An hour would have been perfect for this exam imo.
 

Loki

Count of Concision
Last bump for Boomer-- I saw you on the user list, so I figured I'd see how the test went. :)
 
Loki said:
Oh, and the resonance structure/hyperconjugation stuff wasn't in the readings; in fact, it's supposed to be covered in our Nov. 11 lecture, according to my lecture outline. It was just mentioned briefly for about 30 seconds. What a weirdo my professor is. :p
whoops :p
Are you in orgo now, eggplant? Or have you taken it recently? I'm just curious as to how long it would take you (or anyone) to do the first question in particular. Believe me-- the test is fair enough, but to do it in under 50 minutes puts you in a pinch. An hour would have been perfect for this exam imo.

I finished ochem Spring 2003. My prof let us use models in class so the first one wouldn't be hard.

As for the first quesetion, hmmm. It's been a while since ochem, but I get the gist of what they want. I'd probably draw it out in plain line angle notation first to think up the possiblites of puttin the other groups. Then I'd do the R/S deal. Yeah stereochemistry plays with your mind.
 

Loki

Count of Concision
eggplant said:
whoops :p


I finished ochem Spring 2003. My prof let us use models in class so the first one wouldn't be hard.

As for the first quesetion, hmmm. It's been a while since ochem, but I get the gist of what they want. I'd probably draw it out in plain line angle notation first to think up the possiblites of puttin the other groups. Then I'd do the R/S deal. Yeah stereochemistry plays with your mind.

Yeah, that's how you'd go about it, and how I did as well. Thing is, it's a relatively complex molecule with numerous substituents. So I drew out the "normal" skeleton, then converted that into a Fischer projection (which you have to be careful about, since you have to assume a uniform perspective when looking at the molecule), then converted it into the Newman Projection. Keep in mind that you have to group several substituents together for each "spoke" on the Newman Projection, since there are more groups than spokes; this also takes time in order to be able to express it correctly, nomenclature and bond-wise. It was just a pain in the ass; if there's a simpler way to do these things, we never learned it (which I think there is-- I did some snooping about online and found a site that details how to put molecular formulas into Fischer diagrams effortlessly; unfortunately, we were never taught these "rules", we just had to assume a perspective and place the substituents accordingly; when there's a shitload of substituents, you're screwed, especially upon converting to the Newman Proj.). And then there's the R/S designation to make sure about. I didn't get it wrong, but it took me a bit of time, which was my whole point-- 50 minutes for this test was a bit rushed imo.


What do you mean "let you use models in class"? You brought your own in? He recommended a model set for us, but we wouldn't be able to bring it into lecture and ask questions with it lol. Maybe you could bring it to his office during office hours, though. :p
 
Loki said:
Yeah, that's how you'd go about it, and how I did as well. Thing is, it's a relatively complex molecule with numerous substituents. So I drew out the "normal" skeleton, then converted that into a Fischer projection (which you have to be careful about, since you have to assume a uniform perspective when looking at the molecule), then converted it into the Newman Projection. Keep in mind that you have to group several substituents together for each "spoke" on the Newman Projection, since there are more groups than spokes; this also takes time in order to be able to express it correctly, nomenclature and bond-wise. It was just a pain in the ass; if there's a simpler way to do these things, we never learned it (which I think there is-- I did some snooping about online and found a site that details how to put molecular formulas into Fischer diagrams effortlessly; unfortunately, we were never taught these "rules", we just had to assume a perspective and place the substituents accordingly; when there's a shitload of substituents, you're screwed, especially upon converting to the Newman Proj.). And then there's the R/S designation to make sure about. I didn't get it wrong, but it took me a bit of time, which was my whole point-- 50 minutes for this test was a bit rushed imo.

lol I've forgotten about Fischer projection. Now that one was a pain.

What do you mean "let you use models in class"? You brought your own in? He recommended a model set for us, but we wouldn't be able to bring it into lecture and ask questions with it lol. Maybe you could bring it to his office during office hours, though. :p

you know, the ball and stick things that let you create models of the molecules. So you can rotate them around, add different groups, etc. IIRC, you can go straight from model to Newman projection.
 

Loki

Count of Concision
eggplant said:
lol I've forgotten about Fischer projection. Now that one was a pain.

Indeed-- especially when there are multiple chiral centers. :p


you know, the ball and stick things that let you create models of the molecules. So you can rotate them around, add different groups, etc. IIRC, you can go straight from model to Newman projection.

No, I didn't ask "what are models?" :D, I asked if you meant that he allowed you to bring them to lecture/exams? That's crazy (and great) if he did, though, as it would help a lot (though they're a bit cumbersome, if you ask me). I personally didn't buy a model set despite it being recommended on our syllabus (along with $250 worth of other texts and supplements-- I'll pass on the extra expense, thankyouverymuch :p), though some of my classmates did; reactions have been mixed, and their utility has yet to be determined. Some guys love 'em, some hate 'em.
 
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