Dismiss Notice
Join Physics Forums Today!
The friendliest, high quality science and math community on the planet! Everyone who loves science is here!

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


    User Avatar
    Science Advisor
    2017 Award

    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.
Know someone interested in this topic? Share this thread via Reddit, Google+, Twitter, or Facebook