Properties of -COOR functional group?

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The discussion centers on the electronic effects of the COOR group in organic chemistry, specifically its inductive and resonance effects. The COOR group is identified as an electron-withdrawing group, exhibiting a weaker +I effect compared to stronger groups like COOH and SO3H. While it does not show resonance due to the O-R bond, it is suggested that the C=O bond contributes to a resonance effect, making COOR a meta-directing group in electrophilic substitutions on aromatic compounds. Additionally, alpha-beta unsaturated esters are noted to undergo addition at the beta position, further indicating the resonance influence of the C=O bond.
kay
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By properties I mean the +I or -I effect as compared to other functional groups along with whether it induces a +R or -R effect?
 
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COOR is an electron withdrawing group. But I don't think it shows resonance due to O-R bond.
It is a weaker +I group than COOH and SO3H
 
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AdityaDev said:
COOR is an electron withdrawing group. But I don't think it shows resonance due to O-R bond.
It is a weaker +I group than COOH and SO3H
Thank you. :D
 
I think I was taught COOR was a meta-directing group in electrophylic substitutions on Ar-COOR; and alpha-beta unsaturated esters do undergo addition in beta.
So in theory it does have a 'resonance' effect. Not because of the O-R bond, but because of the C=O bond.
 
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lavoisier said:
I think I was taught COOR was a meta-directing group in electrophylic substitutions on Ar-COOR; and alpha-beta unsaturated esters do undergo addition in beta.
So in theory it does have a 'resonance' effect. Not because of the O-R bond, but because of the C=O bond.
Thank you. :)
 

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