Properties of -COOR functional group?

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SUMMARY

The -COOR functional group is classified as an electron-withdrawing group that exhibits a weaker +I effect compared to COOH and SO3H. It does not show resonance due to the O-R bond; however, it does have a resonance effect attributed to the C=O bond. In electrophilic substitutions on aromatic compounds containing the -COOR group, it acts as a meta-directing group. Additionally, alpha-beta unsaturated esters involving this group undergo addition at the beta position.

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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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