What Are the Effects of Carboxyl Groups on Electron Distribution?

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Discussion Overview

The discussion revolves around the effects of carboxyl groups and other substituents on electron distribution in aromatic compounds, particularly focusing on electron withdrawing and donating groups. Participants explore the implications of these groups on acidity and resonance stabilization in various contexts.

Discussion Character

  • Exploratory
  • Technical explanation
  • Conceptual clarification
  • Debate/contested

Main Points Raised

  • Some participants describe electron withdrawing groups as entities that "suck" electrons from aromatic systems due to their electronegativity.
  • There is a question regarding whether the hydroxyl group (-OH) acts as an electron withdrawing or donating group, with differing views presented based on the context of its attachment.
  • One participant claims that phenol's acidity is due to resonance stabilization of the negative charge formed upon deprotonation of the -OH group, suggesting that the behavior of -OH can vary depending on its environment.
  • Another participant questions the apparent contradiction of -OH being an electron donating group while also enhancing acidity in certain positions on the benzene ring.
  • Clarification is sought on the reference point for discussing the positioning of the -OH group in relation to other functional groups on the benzene ring.

Areas of Agreement / Disagreement

Participants express differing views on the classification of the -OH group as electron withdrawing or donating, and the implications of this classification on the acidity of phenol in different positions. The discussion remains unresolved with multiple competing perspectives.

Contextual Notes

Participants note that the behavior of functional groups can be context-dependent, particularly regarding their electron donating or withdrawing nature, and the discussion highlights the complexity of these interactions in aromatic systems.

pink_ele
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what are electron withdrawing groups?
please give any important advice to solve questions based on it concept.
 
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I like to think electron withdrawing groups as "thirsty suckers". They suck the electrons out of the ring... due to their electronegativity nature.

Take a look at many examples of ewd and electron donating group. You will see the difference. :) Just a pointer to help you: check the bond mulitiplicity in each case. You will find that unsaturated bond exist mostly in one of them.
 
thank you
 
can you tell me whether -OH (hydroxyl group) is electron withdrawing or electron releasing group ?
 
electron withdrawing
 
is phenol acidic due to the presence of an electron withdrawing group .ie -OH group?
 
Phenol is acidic because the negative charge formed from deprotonating the -OH is stabilized by resonance with the aromatic ring.

Whether something is electron withdrawing or electron donating is somewhat context dependent. While -OH acts as an electron withdrawing group when it is attached to an alkyl chain, -OH acts as an electron donating group when attached to an aromatic system (such as in the case of phenol). In the case of aromatic molecules, the lone pair gets donated into the aromatic system, which outweighs the electron withdrawing effect from oxygen's electronegativity.
 
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If OH on a benzene ring is actually an EDG (activating), why is it a strong acid in the meta position, and a weak acid in the para position. I understand activiting groups are O/P directing- I just don't see why OH would enhance the acidity of a benzene ring at all, if it is in fact an EDG.
 
When we are discussing about meta/ortho/para positioning, we need a reference point.

What is the functional group on benzene that OH is taken with respect to?
 
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Sorry about that, its a Carboxyl group. CO2H
 

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