Stability Order of resonating structures

AI Thread Summary
The discussion centers around the stability of resonance structures of vinyl chloride. The user believes the order of stability should be I>III>II, arguing that structure I is most stable due to having no charge, while structure II is less stable because it features a positively charged chlorine atom, which is electronegative. However, the book states the order as I>II>III, prompting confusion. A key point of contention is the valence electrons of chlorine in structure III, which the user calculates as 10, raising questions about its validity since chlorine can typically hold a maximum of 8 electrons. This leads to the conclusion that structure III may not be a permissible resonance structure based on standard electron capacity rules.
randomgamernerd
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I have uploaded the picture of the structures because I couldn't figure out how to type.
Its vinyl chloride.
15314715716633361855743515196350.jpg

According to me the order should be
I>III>II
because I has no charge so it must be most stable
in II we have Cl an electronegative element bearing positive charge which makes it unstable.
Hence I get the order.
But the book says the order is I>II>III
Please Help
 

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How many electrons are in the valence shell of the Cl in III?
 
mjc123 said:
How many electrons are in the valence shell of the Cl in III?
apparently 10how is that possibleit can hold at max 8 if I'm not wrong
 
So III is not a permissible resonance structure according to the ordinary rules.
 

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