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

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SUMMARY

The reaction of chloromethane with hydroxide ions results in the formation of methanol through the substitution of the chlorine atom by an OH functional group. The substitution occurs because the hydroxide ion is a better nucleophile compared to hydrogen, despite chlorine's higher electronegativity. The concept of leaving groups in organic chemistry explains this phenomenon, as chlorine is a better leaving group than hydrogen, facilitating the reaction. Understanding these principles is essential for grasping nucleophilic substitution mechanisms.

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  • Understanding of nucleophilic substitution reactions
  • Familiarity with electronegativity values and their implications
  • Knowledge of leaving groups in organic chemistry
  • Basic concepts of functional groups and their reactivity
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rudders93
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Hi,

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" ) 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?

Thanks!

EDIT: Please move to homework forum? Not exactly sure where this belongs :(
 
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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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