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More polarised more reactive?

  1. Oct 30, 2015 #1
    For acyl chloride the very electronegative oxygen atom attracts electrons of the carbon atom, thus greatly polarised the C-Cl bond. But won't it attract electrons of the Cl atom too? Then with the electrons drifting towards the C atom, it's partial positive charge should be reduced, but why is that wrong?
    Also, since the C-Cl bond is greatly polarised, the bonding should be stronger, isn't it? Like C-F bond is more polar than C-Cl bond, so the fluoroalkane is less reactive than chloroalkane, but why is that acyl chloride, with its very polarised C-Cl bond, so reactive?
    And for chlorobenzene, the electrons on halogen atom are delocalised into the benzene ring, causing the polarity of C-X bond to decrease, but why is it that the bond is stronger than haloalkane?
    I realise that this is a very long question, thank you for your patience
     
  2. jcsd
  3. Oct 30, 2015 #2

    Borek

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    Staff: Mentor

    Chlorine electronegativity is not much lower than that of oxygen.
     
  4. Oct 31, 2015 #3
    I don't understand
     
  5. Nov 1, 2015 #4

    Borek

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    Staff: Mentor

    You can't assume oxygen draws the electrons from the carbon, and chlorine doesn't.
     
  6. Nov 1, 2015 #5
    Ohhh, I got it
    But what about the next question? I thought the more polarised a bond is, the stronger it is, so it's less reactive?
     
  7. Nov 1, 2015 #6
    Both C=O or C-O and C-Cl are polarized, Oxygen does attract e from Carbon towards itself, and so does Chloride, which leaves the positively charged carbon atom to be easily attacked by nucleophiles (e.g water).
     
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