dentalmagnet

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I have the 2007-2008 edition of the Kaplan DAT book. On page, 680 #92. Does anyone else think this question is wrong? The answer they give is E which has carbon with 5 bonds! outrageous right? lol...please if you are good at organic and you have this book sitting in your room, open it and let me know what you think. Thank you so much!!
 

joedat41

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Carbon can't have 5 bonds. I have the Kaplan book but not with me right now. I will check later for you
 

dentalmagnet

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Carbon can't have 5 bonds. I have the Kaplan book but not with me right now. I will check later for you
oh yeah..the explanation does not even make sense. They say C is wrong because the carbonyl only has 3 bonds...but in the picture, the carbonyl has four bonds! I just want to see if anyone can show me something I'm not seeing. Thanks Joedat41!
 
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zuma35

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You're right. Both C-O bonds should really be single bonds.
 

dentalmagnet

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You're right. Both C-O bonds should really be single bonds.
Did you look in the kaplan book? Did you notice that too? I'm taking it into my organic professor on Monday because it's bothering me. Such a simple question, such a very wrong answer. Carbon never has 5 bonds!!
 

zuma35

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One of many mistakes in Kaplan. Don't let it trouble you too much.
 

dentalmagnet

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DAT Kaplan blows... I have the book and I think it is a typo of some kind, you are right.

Thanks for the response. Yeah Kaplan is really easy. I am going to stick to Destroyer from now on. It's like 300x harder..
 

Sublimation

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I have the 2007-2008 edition of the Kaplan DAT book. On page, 680 #92. Does anyone else think this question is wrong? The answer they give is E which has carbon with 5 bonds! outrageous right? lol...please if you are good at organic and you have this book sitting in your room, open it and let me know what you think. Thank you so much!!
That is not a typo. that is correct. Have you ever seen a resonance structure with a combined representation? all they are showing you as that the electrons get delocalized along those bonds. That answer seems perfectly correct to me. Look at it again and draw the lone pairs on the N and draw out the triple bonds in the aromtic ring agian, and you will see that the representation fits perfectly. Chemists usually denote a resonance stabalized bond as such
(check attachment)
 

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Sublimation

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Did you look in the kaplan book? Did you notice that too? I'm taking it into my organic professor on Monday because it's bothering me. Such a simple question, such a very wrong answer. Carbon never has 5 bonds!!
I would agree that the way they chose to represent the "correct" answer was incorrect in itself. there should be only one negative charge on one o fhthe two oxygen atoms. The one with the double bond should be neutral, and if you are using the parameters they are using for representing a delocalized bond, then you will need to draw "six"bonds on the carbon you are referring to. That is one of MANY poorly represented answer choices, i hope the real DAT is not like that. Gluck I will draw out the Correct representation of this molecule for you. I will post it by tomorrow.
 

dentalmagnet

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Thank you for your detailed response. I see what you are saying..but I'm not sure that this particular answer means that. I mean, wouldn't they use a dashed line along with the bold line? I see that one bond may be considered shorter than the other..but they drew that for the C-N bond as well. I don't know.
 

dentalmagnet

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Here it is.

haha thanks! Your drawings are correct by my standards..theirs aren't There is an extra bond to only one of the carbonyls. Me thinks they are dumbies..smarter than me..but still dumbies!
 

dentalmagnet

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;;
 
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Sublimation

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sublim, are you taking organic II right now..or did you already take it? I see you are in Tampa, me too..at USF?
Im taking it next semester with Dr. BAKER!!!! lol that guy is such a douch. He isnt hard by any means, just very rude, and condescending
 

zuma35

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You guys are reading way too much into this. They did not intend any combined representation or anything. It's a simple typo. There should only be a single bond between the C-O.
 

dentalmagnet

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;
 
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dentalmagnet

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You guys are reading way too much into this. They did not intend any combined representation or anything. It's a simple typo. There should only be a single bond between the C-O.
I agree. It's whack lol.
 
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