Stability Order of resonating structures

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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.
Textbook illustration 4.18 asking to order three resonance structures of vinyl chloride by decreasing stability, showing CH2=CH-Cl(:) (I), :CH2-CH=Cl(+) with negative charge on carbon (II), and CH2(+)-CH=Cl(:) with negative charge on chlorine (III).

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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  • Textbook illustration 4.18 asking to order three resonance structures of vinyl chloride by decreasing stability, showing CH2=CH-Cl(:) (I), :CH2-CH=Cl(+) with negative charge on carbon (II), and CH2(+)-CH=Cl(:) with negative charge on chlorine (III).
    15314715716633361855743515196350.jpg
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Discussion

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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