Jochi1543 Posted November 2, 2006 Report Share Posted November 2, 2006 Just got out of an o-chem midterm and I'm in agony over the one question I spent 30+ minutes trying to figure out, even though I had no problem with other questions of this type on the same exam. He wanted us to come up with a ketone that had NO primary carbons and had a formula of C4H8O2. I eventually gave up, but I'm still agonizing over it and can't find anything like that on Google. Maybe someone here will end my agony by telling me what it would look like? I thought that to have no primary carbons, this molecule would have to have a ring structure to it, but the basic ring is C4H8 so after adding the double-bond oxygen to make it a ketone 2 hydrogens would have to leave, and then there's also the second oxygen to be put somewhere, so it didn't really work. Any takers? Link to comment Share on other sites More sharing options...
FireDragoonX Posted November 2, 2006 Report Share Posted November 2, 2006 removed... Link to comment Share on other sites More sharing options...
avenir001 Posted November 2, 2006 Report Share Posted November 2, 2006 ...uh that seems pretty easy 2-one-butanol seems to work if theres an alcohol group otherwise, CH3COCH2-O-CH3 (an ether compound) no, this one has two primary carbons... I think there might be a typo in the question...with an unsaturation number of 1 (which accounts for the carbonyl double bond), I don't see how you could avoid having a primary carbon. Maybe the formula was meant to be C4H6O2 or something like that? Link to comment Share on other sites More sharing options...
UBCGuy Posted November 2, 2006 Report Share Posted November 2, 2006 No... Haha, I think that either there is a problem with the question or you don't remember it perfectly. I racked my brain but couldn't come up with any 'tricks' to make this work. Hope it doesn't haunt you too much! UBCGuy Link to comment Share on other sites More sharing options...
The Law Posted November 2, 2006 Report Share Posted November 2, 2006 Yeah, I couldn't get it to work either. Link to comment Share on other sites More sharing options...
FireDragoonX Posted November 2, 2006 Report Share Posted November 2, 2006 removed... Link to comment Share on other sites More sharing options...
White-Tiger Posted November 2, 2006 Report Share Posted November 2, 2006 and thats why i got B- on Org2 Link to comment Share on other sites More sharing options...
Smurfette Posted November 2, 2006 Report Share Posted November 2, 2006 Are you sure that it's a ketone? If it simply said it was a carbonyl, then it could be a straight chain with an aldehyde on one end and an alcohol on the other. Link to comment Share on other sites More sharing options...
Jochi1543 Posted November 2, 2006 Author Report Share Posted November 2, 2006 Are you sure that it's a ketone? If it simply said it was a carbonyl, then it could be a straight chain with an aldehyde on one end and an alcohol on the other. No, I re-read the question 30 times on the exam thinking "no way" and yes, it's correct. I also thought he made a mistake in the question. I haven't had a chance to talk to anyone else in my class yet, I wonder whether anyone was able to answer it. Link to comment Share on other sites More sharing options...
Gadzillar Posted November 2, 2006 Report Share Posted November 2, 2006 If you consider epoxides as a kind of ketone you can do it...but I'm not sure if that's even close to what he wants. Link to comment Share on other sites More sharing options...
avenir001 Posted November 3, 2006 Report Share Posted November 3, 2006 Epoxides as a kind of ketone?...and what would such epoxidic ketones:D look like? C'mon you guys...you're making me feel like an o-chem expert which I know I'm not...but hey, it's good for my ego:D Link to comment Share on other sites More sharing options...
Darla Posted November 3, 2006 Report Share Posted November 3, 2006 Is anyone else incredibly proud of Jochi? She's gone from being incredibly frustrated by organic http://www.premed101.com/forums/showthread.php?t=7011 to finding typos on her midterms. I hope I don't sound patronizing, I just think this is great for you!! Link to comment Share on other sites More sharing options...
The Law Posted November 3, 2006 Report Share Posted November 3, 2006 Yay for Jochi!!! Link to comment Share on other sites More sharing options...
UBCGuy Posted November 3, 2006 Report Share Posted November 3, 2006 Are you sure that it's a ketone? If it simply said it was a carbonyl, then it could be a straight chain with an aldehyde on one end and an alcohol on the other. This system would still have 2 primary carbons. Primary, secondary, tertiary, and quaternary are indications of how many other carbons the carbon in question is bonded to. A C-O bond (or C=O bond) is not taken into consideration . Link to comment Share on other sites More sharing options...
avenir001 Posted November 3, 2006 Report Share Posted November 3, 2006 Is anyone else smelling some love in the air? Joking aside, good job Jochi!...we are proud of you. Link to comment Share on other sites More sharing options...
Jochi1543 Posted November 3, 2006 Author Report Share Posted November 3, 2006 Lol, whatever guys.... I have the lecture in 15 mins, he better not have graded the exams already...I'd rather spend my weekend in ignorance (and bliss). Link to comment Share on other sites More sharing options...
Gadzillar Posted November 3, 2006 Report Share Posted November 3, 2006 Epoxides as a kind of ketone?...and what would such epoxidic ketones:D look like?C'mon you guys...you're making me feel like an o-chem expert which I know I'm not...but hey, it's good for my ego:D Well no, I mean obviously it isn't, but there's still the oxygen with two bonds to carbon, it's just that they're different carbons! And yes, that does sound stupid to me when I write it out. Come to think of it, an epoxide is closer to a weird ether than a weird ketone. Link to comment Share on other sites More sharing options...
Jochi1543 Posted November 3, 2006 Author Report Share Posted November 3, 2006 We haven't even gotten around to epoxides yet, so I doubt that's what's expected.... He didn't have them graded yet (phew!). Link to comment Share on other sites More sharing options...
Tim Posted November 5, 2006 Report Share Posted November 5, 2006 Is a carbon bonded to one other carbon and an oxygen still considered a primary carbon? Link to comment Share on other sites More sharing options...
The Law Posted November 5, 2006 Report Share Posted November 5, 2006 Is a carbon bonded to one other carbon and an oxygen still considered a primary carbon? Yes it is... any carbon bonded to one other carbon is a primary. Link to comment Share on other sites More sharing options...
Jochi1543 Posted November 6, 2006 Author Report Share Posted November 6, 2006 OK, he admitted that it was a mistake. Link to comment Share on other sites More sharing options...
TimmyMax Posted November 7, 2006 Report Share Posted November 7, 2006 Hey, Good to know- I was starting to question my organic chem prowess for a second there! Link to comment Share on other sites More sharing options...
The Law Posted November 7, 2006 Report Share Posted November 7, 2006 I'm not sure if this works, but what about: 1,2 - Cyclobutanol? C-C-OH | | C-C-OH and the C's filled with H's... the ring counts for the one unit of saturation. If somebody else already mentioned that, then 2 people confirm it! muahaha Link to comment Share on other sites More sharing options...
JOTCH Posted November 7, 2006 Report Share Posted November 7, 2006 he said KETONE... Link to comment Share on other sites More sharing options...
avenir001 Posted November 7, 2006 Report Share Posted November 7, 2006 Yeah it would help to read the question before attempting to answer:D Link to comment Share on other sites More sharing options...
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