basicity and Keq

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Unlearner

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"which of the following molecules will react with H2SO4 and have the highest Keq for the reaction?"
a) CH3CONH2
B) CH3CH2NH2
C) (CH3CH2)2NH2
D) C5H6NH2

the answer was 'c' What's the best way to break this down in order to figure out which is the most basic?
 
The answer will be the molecule that is the most basic, or the one that has the greatest ability to donate electron density.

a) CH3CONH2 --> The CO represents a carbonyl group and the adjacent N exhibits resonance with the C=O double bond, delocalizing the electrons and making this molecule's ability to donate electron density worse. Probably not your answer.
B) CH3CH2NH2 --> This answer is okay. The N has two lone pairs and there is no electron delocalization. Maybe
C) (CH3CH2)2NH2 --> This answer is better than the last group because it is more substituted. As you know, alkyl groups donate electron density so because this one has more alkyl groups, the N in this case will have more electron density than in B. Better answer.
D) C5H6NH2 --> The N in this case exhibits resonance with the benzene ring it is attached to. For the same reasoning in A, this is probably not your best answer.

Therefore, because the N in C can donate the most electron density, it is your best answer.

Hope this helps.
 
C... Because, it has the biggest delta positive. Nitrogen is getting all the e- density sucked out of it.

Correct me if I am wrong, please.
 
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