BruceWayne Posted May 25, 2012 Report Share Posted May 25, 2012 Why is the order in the title the order for acidity when I've also been told that longer bonds are more acidic since they are weaker, so H can leave more easily? And isn't sp bonds the smallest? Thanks Link to comment Share on other sites More sharing options...
thehumanmacbook Posted May 25, 2012 Report Share Posted May 25, 2012 Hi Batman, http://forums.studentdoctor.net/showthread.php?t=776086 Is a very succint answer. Link to comment Share on other sites More sharing options...
lysine Posted May 25, 2012 Report Share Posted May 25, 2012 S orbitals hold their electrons more tightly than p orbitals, it is harder to distort an s orbital than a p orbital. S orbitals hold the electrons closer to the nucleus than a p orbital, so s orbitals are able to better stabilize a negative charge. So the more s character a carbon has, the more acidic it is. So sp > sp2 > sp3 (50% s > 33% s > 25% s) for acidity because a negative charge on an sp hybridized carbon is held closer to the nucleus by its higher s character and so the charge is more stabilized. Link to comment Share on other sites More sharing options...
BruceWayne Posted May 25, 2012 Author Report Share Posted May 25, 2012 Lol that link you gave me is the exact reason I asked this. Thanks, it makes sense now. Link to comment Share on other sites More sharing options...
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