Properties of -COOR functional group?

Click For Summary

Discussion Overview

The discussion centers on the properties of the -COOR functional group, specifically its inductive (+I or -I) and resonance (+R or -R) effects compared to other functional groups. Participants explore theoretical implications in the context of electrophilic substitutions and reactivity in organic chemistry.

Discussion Character

  • Technical explanation
  • Debate/contested

Main Points Raised

  • Some participants propose that the -COOR group is an electron-withdrawing group but question its resonance contribution due to the O-R bond.
  • Others argue that -COOR is a weaker +I group compared to COOH and SO3H.
  • A participant mentions that -COOR is considered a meta-directing group in electrophilic substitutions and suggests that it has a resonance effect attributed to the C=O bond rather than the O-R bond.

Areas of Agreement / Disagreement

Participants express differing views on the resonance effects of the -COOR group and its classification as a meta-directing group, indicating that multiple competing perspectives remain in the discussion.

Contextual Notes

There are unresolved questions regarding the extent of resonance and inductive effects, as well as the definitions of terms used in the discussion.

kay
Messages
60
Reaction score
2
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?
 
Chemistry news on Phys.org
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
 
  • Like
Likes   Reactions: kay
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.
 
  • Like
Likes   Reactions: kay
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. :)
 

Similar threads

(S)-2,3- Dihydroxypropanal priority
  • · Replies 5 ·
Replies
5
Views
2K
Why Does Reactivity Differ in Group 7?
  • · Replies 2 ·
Replies
2
Views
2K
Glycolic acid functional group(s)
  • · Replies 3 ·
Replies
3
Views
3K
Function Group vs. Mechanisms approach (Organic Chemistry)
  • · Replies 1 ·
Replies
1
Views
4K
Undergrad Phase and group velocity for the wave function
  • · Replies 14 ·
Replies
14
Views
4K
Naming the pentane with phenyl group (or benzene with aryl group)
  • · Replies 1 ·
Replies
1
Views
2K
Common Reducing Agents & Incompatible Functional Groups
  • · Replies 1 ·
Replies
1
Views
2K
Implementing “Ab initio” approach in molecular mechanics method
  • · Replies 4 ·
Replies
4
Views
2K
Interesting compounds with alcohol functional group
  • · Replies 6 ·
Replies
6
Views
2K
Graduate How Can I Compare Parton Distribution Functions Without Data from Other Groups?
  • · Replies 4 ·
Replies
4
Views
3K