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Topic: Are the Sp3 orbital is a stronger base than the sp2 atom?  (Read 12347 times)

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Offline jinclean

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Are the Sp3 orbital is a stronger base than the sp2 atom?
« on: October 27, 2009, 06:33:13 AM »
In the C=0 bonds ,in my textbook .it says that the sp3 is more active to be protonized than the C-O bond .but why in the C=N is less basic than the C-N bond?

Offline Schrödinger

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Re: Are the Sp3 orbital is a stronger base than the sp2 atom?
« Reply #1 on: October 27, 2009, 03:10:53 PM »
sp2 hybridized atoms are more electronegative than sp3 hybridized ones due to greater s-character. So, the sp2 atoms tend to keep the unshared pair of electrons to themselves rather than giving them away to an acid's proton.
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Offline jinclean

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Re: Are the Sp3 orbital is a stronger base than the sp2 atom?
« Reply #2 on: October 28, 2009, 07:25:34 AM »
Thack you for your reply,
but the C=O is more basic than the R-O-R',it is oppose to this conclusion   

Offline lancenti

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Re: Are the Sp3 orbital is a stronger base than the sp2 atom?
« Reply #3 on: October 28, 2009, 10:47:18 AM »
You may want to also consider the lack of a resonance structure when an ether acts as a base as opposed to a carbonyl group acting as a base.

Then there's also steric hindrance to consider, since if the R-groups are so bulky that they protect the lone pairs.

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