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Topic: Which of the two protons are more acidic?  (Read 2193 times)

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Offline ZekR

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Which of the two protons are more acidic?
« on: March 31, 2013, 08:28:02 PM »
I have just started studying organic chemistry and there is a question in the book that I do not understand how they got the answer.  The question is "For each of the following compounds, two protons have been highlighted.  In each case, determine which proton is more acidic" and the compound in question is attached.

According to the book the correct answer is the left proton, but I do not see how that is. From what I can tell, the conjugate base for both the left and the right proton are on a carbon atom and they both have two resonance structures.  But the right proton also has inductance from the nitrogen atom, so isn't the conjugate base for the right proton more stable, and thus that proton more acidic?

To show my reasoning, I have attached diagrams of both scenarios. 

If someone could explain this to me in simple terms, it would be great.

Thanks.

Offline ZekR

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Re: Which of the two protons are more acidic?
« Reply #1 on: March 31, 2013, 08:38:01 PM »
Just as I posted the question, I got it (I think):  the left proton is more acidic because the charge is spread out over both a carbon and a nitrogen atom in its resonance structures, while with the right proton, the charge is spread out over two carbon atoms.  But please correct me if I am missing something.

Offline argulor

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Re: Which of the two protons are more acidic?
« Reply #2 on: April 01, 2013, 01:26:31 AM »
Just as I posted the question, I got it (I think):  the left proton is more acidic because the charge is spread out over both a carbon and a nitrogen atom in its resonance structures, while with the right proton, the charge is spread out over two carbon atoms.  But please correct me if I am missing something.

Right answer, but I would rationalize it by saying negative charge on N (more electronegative) is more stable than negative chargen on C.

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