sp2 hybridization implies adjacent sp2 hybridization?

[Teleologist]

Is this true? Let me know if I"m the only person who's learned this "rule."

If this is true then why is the chlorine in chlorate anion sp3 hybridized?

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[TheRelevant]

I've never heard of this rule either. But it definitely makes sense in the context of resonance-induced sp2 hybridization. However, there are still atoms like boron which will have sp2 hybridization without having pi-bonds (and therefore will not cause their neighbouring atom with a lone pair to undergo resonance). So I am not too confident about this "rule" either.

 

[pharmolu]

yea that's not true. Other examples include amides and esters.

 

[Teleologist]

yea that's not true. Other examples include amides and esters.

You sure about that? Everything in an amide is sp2 hybridized.

 

[TheRelevant]

Yeah amides are definitely sp2 hybridized. Do the -O- (the ethers) in esters have sp2 hybridization as well?

 

[pharmolu]

You sure about that? Everything in an amide is sp2 hybridized.

You're definitely correct, sorry about that. Also esters don't seem to work either. I think their example work however if you assume the octet rule and the atom is connected to carbon, because then a lone is in a conjugated system with the double bond.

also, I'm not sure about this, but what about an oxmide? is the oxygen sp2 hybridized?

 

[TheRelevant]

The oximes would have resonance. But it would create a fairly unstable resonance structure (positive formal charge on oxygen and a lone pair on a carbon). So I am not sure if that resonance structure even contributes enough to cause sp2 hybridization. I am leaning towards yes. In any case, aldoxime would be the more stable structure as it would have the less substituted carbanion