October21PODkey - electron density and negative charge on N...

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October 21, 2009 Problem-of-the-Day Is the following molecule more likely to get protonated on O or N? Explain your reasoning. Chem 128A, Fall 2009 O N O N O N O-protonation is more likely. The most reasonable resonance structures for this molecule involve an increase of electron density and negative charge on the O and a decrease of
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Unformatted text preview: electron density and negative charge on N (relative to the top structure). This implies that the overall resonance hybrid that is this molecule will have a relatively electron rich O and relatively electron poor N (the more electron rich something is, the more likely it is to grab a proton)....
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This note was uploaded on 02/22/2010 for the course CHE che110b taught by Professor Franics during the Spring '10 term at Concord.

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