bond strength and hybridization

[Ton1c]

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In early ochem chapters of TBR it says "The more s-character in the hybrid orbital of the atom bonded to hydrogen, the stronger the acid" (pg 19) so in terms of acidity sp>sp2>sp3
this means that C-H bond strength is sp3>sp2>sp?

because in the IR spectroscopy chapter (pg 111) it says "The result is that an sp2-C-to-H bond is shorter and thus stronger than an sp3-C-to-H bond"

can anyone clarify?

Thanks🙂

 

[Gauss44]

In early ochem chapters of TBR it says "The more s-character in the hybrid orbital of the atom bonded to hydrogen, the stronger the acid" (pg 19) so in terms of acidity sp>sp2>sp3
this means that C-H bond strength is sp3>sp2>sp?

because in the IR spectroscopy chapter (pg 111) it says "The result is that an sp2-C-to-H bond is shorter and thus stronger than an sp3-C-to-H bond"

can anyone clarify?

Thanks🙂

I think the following is inaccurate, "C-H bond strength is sp3>sp2>sp."

 

[ouroboros39]

Bond strength is not correlated with acidity. Think about how Na-Cl is a very strong bond, but is easily dissociated in water. What they were trying to say was that the more similar the orbital of the carbon attatched to the hydrogen, the stronger the bond. So sp has a stronger Hydrogen Carbon bond because the sp orbital has 50% s character and 50% p character (the hydrogen is 100% s). This results in better overlap and a closer association of the Carbon and Hydrogen ( a very short bond too).

The reason sp carbons are more acidic is because they are more electronegative, since the sp orbital has more s character, it can hold/pull its electrons closer to its nucleus which stabilizes it when it is an anion.

 

[Ton1c]

That makes sense thanks!