June 18, 2021, 10:55:51 PM
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Topic: Lithation of 2-chloropyridine with LDA  (Read 150 times)

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Offline retrospect3

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Lithation of 2-chloropyridine with LDA
« on: May 21, 2021, 05:28:55 AM »
So I was completing the mechanism with the lithation of 2-chloropyridine with LDA and through research I found that the proton at the C-3 position is removed to allow for a nucleophillic attack at the C-3 position. But I'm confused on why the proton is removed rather than Chlorine since chlorine is extremely electronegative.

Essentially, just asking why is the proton at C-3 removed rather than the chlorine


Offline Orcio_Dojek

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Re: Lithation of 2-chloropyridine with LDA
« Reply #1 on: May 21, 2021, 01:43:16 PM »
Quote
I found that the proton at the C-3 position is removed to allow for a nucleophillic attack at the C-3 position
Removing of C-3 H+ will disable nucleophilic substition at this place (Nu- will not attach to C-).

LiN[CH(CH3)2]2 is strong base so substition follows rather elimination-addition mechanism (product will be mixture of 2- and 3-substituted pyridine).
« Last Edit: May 21, 2021, 05:20:21 PM by Orcio_Dojek »

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