Schotten Baumann reaction mechanism
Hey,
I need to show the reaction mechanism of a schotten baumann reaction.
Now I have looked around and managed to find a diagram showing it, but some bits didn't make sense to me, so would someone be able to explain what is actually happening i.e. what is actually happening in each step?
Thanks
I need to show the reaction mechanism of a schotten baumann reaction.
Now I have looked around and managed to find a diagram showing it, but some bits didn't make sense to me, so would someone be able to explain what is actually happening i.e. what is actually happening in each step?
Thanks
Ok here's a diagram
What bit's do you find confusing?
What bit's do you find confusing?
Original post by EierVonSatan
Ok here's a diagram
What bit's do you find confusing?
What bit's do you find confusing?
Okay yeah thats the diagram I found. What's happening in the first step, with the arrow from on side of the C=O double bond to the other?
EDIT:
And
The last/ penultimate step, where the arrow is leaving the nitrogen with a cross through it?
(edited 13 years ago)
Original post by ManicMetalhead
Okay yeah thats the diagram I found. What's happening in the first step, with the arrow from on side of the C=O double bond to the other?
It's a short hand for attack of the amine into the C=O, formation of the tetrahedral intermediate then elimination of the chloride ion. It can be drawn in two steps:
edit: the reaction line with a cross through it means ''no reaction''
(edited 13 years ago)
Okay thanks
And what is actually happening in the last step then?
Is it essentially a repeat of the first step?
Original post by EierVonSatan
edit: the reaction line with a cross through it means ''no reaction''
And what is actually happening in the last step then?
Is it essentially a repeat of the first step?
Original post by ManicMetalhead
And what is actually happening in the last step then?
Is it essentially a repeat of the first step?
Is it essentially a repeat of the first step?
The point of the second line is to say that the acid produced in the first line can inhibit the reaction. Another amine picks up the proton and then can't react with the acyl chloride - so base is added to free the amine up. This amine can then react with an acyl chloride as given in the the first line
Original post by EierVonSatan
The point of the second line is to say that the acid produced in the first line can inhibit the reaction. Another amine picks up the proton and then can't react with the acyl chloride - so base is added to free the amine up. This amine can then react with an acyl chloride as given in the the first line
Oh I see now
Thanks man Quick Reply
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