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

  • Thread starter Thread starter rudders93
  • Start date Start date
  • Tags Tags
    Reaction
AI Thread Summary
Chloromethane reacts with hydroxide ions to form methanol through a substitution reaction where the chlorine atom is replaced by a hydroxyl (OH) group. The confusion arises from the electronegativity values of chlorine and hydrogen, with chlorine being more electronegative than hydrogen. However, the key factor in this reaction is the concept of leaving groups in organic chemistry. Chlorine is a better leaving group than hydrogen due to its ability to stabilize the negative charge after leaving, making it easier for the hydroxide ion to substitute it rather than hydrogen. Understanding the role of leaving groups clarifies why the substitution occurs at the chlorine atom instead of the hydrogen.
rudders93
Messages
46
Reaction score
0
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 :(
 
Last edited by a moderator:
Chemistry news on Phys.org
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.
 

Thread 'Solubility of MgSO47H2O in water'

It seems like a simple enough question: what is the solubility of epsom salt in water at 20°C? A graph or table showing how it varies with temperature would be a bonus. But upon searching the internet I have been unable to determine this with confidence. Wikipedia gives the value of 113g/100ml. But other sources disagree and I can't find a definitive source for the information. I even asked chatgpt but it couldn't be sure either. I thought, naively, that this would be easy to look up without...
View full post »

Thread 'Why does having 8 valence electrons make an element inert?'

I was introduced to the Octet Rule recently and make me wonder, why does 8 valence electrons or a full p orbital always make an element inert? What is so special with a full p orbital? Like take Calcium for an example, its outer orbital is filled but its only the s orbital thats filled so its still reactive not so much as the Alkaline metals but still pretty reactive. Can someone explain it to me? Thanks!!
View full post »

Similar threads

Why is C-Cl bond in acyl chloride more reactive despite being highly polarized?
Replies
5
Views
2K
Why HCl is a much stronger acid than H2O?
Replies
8
Views
17K
Why does an alkoxide steal H from water?
Replies
11
Views
3K
Substitution vs Elimination on halides
Replies
1
Views
2K
Why Do Acids Donate Protons and Not Electrons?
Replies
10
Views
21K
Why does each element only react with certain elements?
Replies
3
Views
3K
Why Does Chlorine Gas Form at the Anode in the Chlor-Alkali Process?
Replies
3
Views
3K
Chemical Reactions: Stronger Bonds, Reactive Elements
Replies
7
Views
4K
Free Radical reaction of methane and Chlorine
Replies
8
Views
2K
Chemistry Identifying the mistake in this reaction scheme to form 2-hydroxyisobutyramide
Replies
6
Views
2K

Hot Threads

Recent Insights

Back
Top