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Reaction of chloroalkane. Why chlorine substituted by OH rather than H

  1. May 6, 2010 #1

    I'm abit confused with how this following example works:

    Chloromethane reacted with hydroxide ion forms methanol as the chlorine atom is substituted by an OH functional group.

    I was wondering why is the chlorine substituted rather than the hydrogen. I get why the OH group substitutes with Cl (since O is more electronegative), but the thing is, Cl is more electronegative (value 3.16 according to http://en.wikipedia.org/wiki/Electronegativity" [Broken]) than H (which has a value of 2.20).

    So why does this happen? Doesn't Cl have a stronger bond to the Carbon than H does hence it's harder to break?


    EDIT: Please move to homework forum? Not exactly sure where this belongs :(
    Last edited by a moderator: May 4, 2017
  2. jcsd
  3. May 6, 2010 #2


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    You should probably read up on leaving groups in an organic chemistry textbook. That should explain why the OH substitutes the Cl and not the H.
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