Originally Posted by Pay919

Last year the midterm average was quite high, which is why I think the exam was more difficult. Just an idea though, however I have seen similar trends with a lot of courses (hard midterm = easy exam, easy midterm = hard exam)

This years' midterms were pretty fair and quite doable... Capretta said he was expecting avg of low 70's for first one and similar for 2nd one but it turned out lower than he expected..

Originally Posted by SciMania

well our midterms were pretty bad, 67 and 57 averages.

(67 is actually not that bad considering the size of the class)

but he did say in the past the average on the exam has been ~68%, which i think is quite high considering how "brutal" everyone says it was. there is hope

My theory is that everyone who found the exam fair/easy doesn't really talk about it cause they don't want to brag/bring other people down who didn't do so well... while everyone who found it hard is super vocal about it and they basically scare everyone who's about to write the exam.

Maybe it's an indirect way of encouraging others to study harder and prepare better? ...that's what I'm telling myself.

wooooo it's done!!

by the way, the comment about most of the questions requiring you to 'think outside the box' was so true. Like this mechanism question where you had to visualize the compound basically flipping inside out on itself.. it was so trippy. Overall not as murderous as I thought it would be, though. I might post an updated course review later on if I have time/feel like it.

thanks for all the responses! :-)

Originally Posted by marcie

wooooo it's done!!

by the way, the comment about most of the questions requiring you to 'think outside the box' was so true. Like this mechanism question where you had to visualize the compound basically flipping inside out on itself.. it was so trippy. Overall not as murderous as I thought it would be, though. I might post an updated course review later on if I have time/feel like it.

thanks for all the responses! :-)

You figured out the mechanism question? Wow. Good for you! I seriously spent a good half hour on that question. At one point, I actually made a song about it! I just couldn't figure out what reacted with what. I was a bit pissed that we were given such a weird mechanism when we studied so many other mechanisms (aldol, malonic acid, hydrolysis, alkylation, etc.). The mechanisms in our tutorial quetions all seemed to focus on these. Anyway, I put something down, but I think I was just making up my own chemistry. I certainly didn't have any weird flipping out of the molecule going on. Sigh, there go 7 marks down the drain.

I also hated how for the first five MC questions, we had to look up the reagents in that huge list on the front page. Did Capretta do that on purpose so we'd lose time? Again, I spent way too much time on those questions since I had to flip back, consult the ****ing list, and copy out all the damn reagents in the options.

Sigh... At this point, I'm just glad the course is over. What a bad experience it was!

Originally Posted by Revolution1

I also hated how for the first five MC questions, we had to look up the reagents in that huge list on the front page.

What is this "reagents list"?

Originally Posted by Revolution1

You figured out the mechanism question? Wow. Good for you! I seriously spent a good half hour on that question. At one point, I actually made a song about it! I just couldn't figure out what reacted with what. I was a bit pissed that we were given such a weird mechanism when we studied so many other mechanisms (aldol, malonic acid, hydrolysis, alkylation, etc.). The mechanisms in our tutorial quetions all seemed to focus on these. Anyway, I put something down, but I think I was just making up my own chemistry. I certainly didn't have any weird flipping out of the molecule going on. Sigh, there go 7 marks down the drain.

I also hated how for the first five MC questions, we had to look up the reagents in that huge list on the front page. Did Capretta do that on purpose so we'd lose time? Again, I spent way too much time on those questions since I had to flip back, consult the ****ing list, and copy out all the damn reagents in the options.

Sigh... At this point, I'm just glad the course is over. What a bad experience it was!

Lol @ making up a song I had "Friday" stuck in my head the whole time. At least you didn't leave it blank, so you'll hopefully get some part marks. That synthesis question stumped me though. I tried working backwards and ended up with a completely different starting compound (cyclopentanone.. bahah). Also the "provide 15/20 products" was pretty confusing.. it's like, not only do you need to know all the reagents and which functional groups they react with and what products they form... but you also need to know what they don't react with.

Yeah the formatting for the 1st five questions was terrible! I didn't even have time to really think about all the reactions.. all I could do was eliminate the "stupid" options. I had to save that one for the end, haha. Having it done is a huge weight off the shoulders though. On to genetics and biochem!

Originally Posted by Revolution1

You figured out the mechanism question? Wow. Good for you! I seriously spent a good half hour on that question. At one point, I actually made a song about it! I just couldn't figure out what reacted with what. I was a bit pissed that we were given such a weird mechanism when we studied so many other mechanisms (aldol, malonic acid, hydrolysis, alkylation, etc.). The mechanisms in our tutorial quetions all seemed to focus on these. Anyway, I put something down, but I think I was just making up my own chemistry. I certainly didn't have any weird flipping out of the molecule going on. Sigh, there go 7 marks down the drain.

I also hated how for the first five MC questions, we had to look up the reagents in that huge list on the front page. Did Capretta do that on purpose so we'd lose time? Again, I spent way too much time on those questions since I had to flip back, consult the ****ing list, and copy out all the damn reagents in the options.

Sigh... At this point, I'm just glad the course is over. What a bad experience it was!

I thought the exam was difficult for all the wrong reasons, unfortunately.

The mechanism and synthesis were as easy as could be expected - if they were something you had seen before, what's the point of asking it? A regular aldol condensation or an easy synthesis are useless on an exam.

The first 5 MC questions - Capretta always does that, it's a good way to test how well you know your synthesis stuff without making a big deal of it (i.e., without making it written) - but I agree, this part gets annoying with the crapload of reagents to sift through.

The thing that worries me now is that I have a feeling if you do a structure (from the 15/20 ones) even slightly incorrectly it's probably going to be 0 or max 1 out of 2. And a lot of the reducing/condensation ones they seem to say "oh this one, the OH eliminates, you didn't eliminate it? 0/2" and for other ones "oh the OH doesn't eliminate in this one, oops you eliminated it, there's a couple marks off!" or "Oh this reagent reduces just like you thought but you accidentally left a double bond here, there's 2 marks off" even if your structure is correct otherwise.

Originally Posted by Serene

What is this "reagents list"?

see the attachment, it was like that only, well, different reagents (this was from a previous year's midterm). And the question would show a starting material with an arrow pointing to a final product, and the options you have to choose from are a series of 2 or 3 letters. Most annoying question ever

Originally Posted by Alchemist11

I thought the exam was difficult for all the wrong reasons, unfortunately.

The mechanism and synthesis were as easy as could be expected - if they were something you had seen before, what's the point of asking it? A regular aldol condensation or an easy synthesis are useless on an exam.

The first 5 MC questions - Capretta always does that, it's a good way to test how well you know your synthesis stuff without making a big deal of it (i.e., without making it written) - but I agree, this part gets annoying with the crapload of reagents to sift through.

The thing that worries me now is that I have a feeling if you do a structure (from the 15/20 ones) even slightly incorrectly it's probably going to be 0 or max 1 out of 2. And a lot of the reducing/condensation ones they seem to say "oh this one, the OH eliminates, you didn't eliminate it? 0/2" and for other ones "oh the OH doesn't eliminate in this one, oops you eliminated it, there's a couple marks off!" or "Oh this reagent reduces just like you thought but you accidentally left a double bond here, there's 2 marks off" even if your structure is correct otherwise.

What was the correct way of doing the mechanism? What did the acid react with? The alcohol group? What the hell happened next? What were you supposed to do with the ether bits? Of course, I didn't expect to see a straightforward aldol reaction. For instance, the mechanisms in the assignments and tutorials weren't straightforward/easy, but at least you could find some way to how to work them out, since they were analagous to the things we'd learned in class. Maybe I'm just not good at "thinking outside the box", but I do think it was kind of a douchey move to put a brain-teaser worth 7 marks on an exam worth 50 % of the final grade. Haha, I imagined Capretta with a troll face the entire time I was struggling with that question (along with the MC question and the 15/20 question)

The synthesis question wasn't too bad.

Originally Posted by Revolution1

What was the correct way of doing the mechanism? What did the acid react with? The alcohol group? What the hell happened next? What were you supposed to do with the ester bits? Of course, I didn't expect to see a straightforward aldol reaction. For instance, the mechanisms in the assignments and tutorials weren't straightforward/easy, but at least you could find some way to how to work them out, since they were analagous to the things we'd learned in class. Maybe I'm just not good at "thinking outside the box", but I do think it was kind of a douchey move to put a brain-teaser worth 7 marks on an exam worth 50 % of the final grade.

The synthesis question wasn't too bad.

Ummm I don't really remember the question perfectly but I can venture a guess:

You protonate one oxygen, and kick it off whilst forming a double bond with the other one. Then, this carbonyl, can be attacked by the other alcohol in the compound. This forms, I think it was a 6 membered ring, or something like that, and you deprotonate and then you're done.

The beauty of mechanisms is that you don't have to have done it before in order to solve it, nor do you have to have a name for it. Being able to get a mechanism has nothing to do with how much you studied, because it's never going to be an exact replica of an aldol or something of that nature. Instead, it just has to do with whether you've internalized the rules of the system and are able to apply those rules to devise or create things you've never seen before. And I guess that comes with practice.

Originally Posted by Revolution1

What was the correct way of doing the mechanism? What did the acid react with? The alcohol group? What the hell happened next? What were you supposed to do with the ester bits? Of course, I didn't expect to see a straightforward aldol reaction. For instance, the mechanisms in the assignments and tutorials weren't straightforward/easy, but at least you could find some way to how to work them out, since they were analagous to the things we'd learned in class. Maybe I'm just not good at "thinking outside the box", but I do think it was kind of a douchey move to put a brain-teaser worth 7 marks on an exam worth 50 % of the final grade. Haha, I imagined Capretta with a troll face the entire time I was struggling with that question (along with the MC question and the 15/20 question)

The synthesis question wasn't too bad.

I forget how it went exactly, but the first 1 or 2 steps involved hemiacetal hydrolysis. This created a double bond between a positively charged OH group and a carbon, which was attacked by the alcohol at the other end of the compound, to form a 6-membered ring with an oxygen in it. Then there were a couple deprotonation/protonation steps to get to the final product.

Kinda hard to describe but that's how I did it

/edit alchemist beat me to it, haha

For 2OD3 we get nothing like that, we basically have to memorize all the reagents and conditions for every reactions. But it does seem restricted though if you don't recognize that specific reagent.

the mechanism question molecule had an ester bit??? how come on my exam paper the bonds between the carbon and the oxygen were all single?

Originally Posted by Serene

For 2OD3 we get nothing like that, we basically have to memorize all the reagents and conditions for every reactions. But it does seem restricted though if you don't recognize that specific reagent.

I don't think you quite understand the question...you still need to memorize all the reagents and conditions. For this question, you have to fill in the reagents you would use to complete the reaction, but you are limited to only the ones listed.

Originally Posted by Serene

For 2OD3 we get nothing like that, we basically have to memorize all the reagents and conditions for every reactions. But it does seem restricted though if you don't recognize that specific reagent.

Lol well of course, ours is the same way. This is just the first few questions of the MC.

The point Marcie was making is that, the "answers" for the MC would be "h then x then d and f" and it's annoying as hell when each reagent could be like (Ch3Ch2Ch2Ch2MgBr) or something, so you have to write that stuff down on the other page and count carbons and whatever to see if it's right, and there's 5 questions x 5 choices each, so 25 times (if you wanted to be sure) you have to go back to the front page and check all the reagents, and so it takes a lot longer than regular MC questions.
It wasn't difficult per se, just time consuming.