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

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In summary, the conversation discusses the reaction of chloromethane with hydroxide ion to form methanol, where the chlorine atom is substituted by an OH functional group. The question is raised as to why the chlorine is substituted rather than the hydrogen. This is explained by the concept of leaving groups in organic chemistry, which states that the OH group is more likely to substitute the Cl due to its higher electronegativity. This is further supported by the fact that Cl has a stronger bond to carbon compared to H, making it harder to break.
  • #1
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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  • #2
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.
 

1. What is the reaction of chloroalkane?

The reaction of chloroalkane is a substitution reaction where one or more hydrogen atoms in a chloroalkane molecule are replaced by a chlorine atom.

2. Why is chlorine substituted by OH rather than H?

Chlorine is substituted by OH (hydroxyl group) rather than H (hydrogen) because OH is a stronger nucleophile than H. This means that OH has a higher tendency to attack the carbon atom and replace the chlorine atom in the chloroalkane molecule.

3. How does the substitution of chlorine by OH affect the properties of the molecule?

The substitution of chlorine by OH changes the properties of the molecule. OH is a polar group, which makes the molecule more polar and increases its solubility in water. It also makes the molecule more reactive, allowing it to participate in further chemical reactions.

4. What is the mechanism of the substitution reaction of chloroalkane?

The substitution reaction of chloroalkane follows an SN2 (substitution, nucleophilic, bimolecular) mechanism. In this mechanism, the OH group acts as a nucleophile, attacking the carbon atom and displacing the chlorine atom in a single step.

5. Are there any other factors that influence the substitution of chlorine by OH?

Yes, there are several factors that can influence the substitution of chlorine by OH, such as the steric hindrance of the carbon atom, the strength of the carbon-halogen bond, and the nature of the solvent. These factors can affect the rate and efficiency of the reaction.

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