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posted by  ManateeDugong on 6/30/2008 1:49:33 AM  |  status: Closed  

Please help me with comparing Bases

Course Textbook Chapter Problem
Organic Chemistry N/A N/A N/A
Question Details:
Which of the following is the stronger base

H3CO- and H3CNH-

H3CO- and H3COH
ManateeDugong: Glad to help and thanks for helping ;)
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posted by KyleK on 6/30/2008 2:09:58 AM  |  status: Live
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ManateeDugong's comment:
"thank you so much for saving my life + wonderful explanation!!!"
Response Details:
H3CNH- is a stronger base than H3CO-.  Oxygen is more electronegative than nitrogen, so it is less likely to share its lone pairs of electrons and is therefore a weaker base.

H3CO- is a stronger base than H3COH.  An anion has more electrons to share and a driving force to share them (returning to a neutral state), so it is much more nucleophilic and basic than a neutral compound.
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