Comparing Reactivity of Chemical Groups: OH-R to O_4S-R

  • Thread starter Thread starter Chuckj
  • Start date Start date
  • Tags Tags
    Chemical Groups
Click For Summary

Discussion Overview

The discussion revolves around the reactivity of various chemical groups linked to a common position in different substances, specifically comparing groups such as OH-R, ON2-R, O3P-R, and O4S-R. The context includes considerations for both aromatic substitution and nucleophilic substitution reactions.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • Some participants suggest that the reactivity in aromatic substitution is influenced by the nature of the substituents, with more electronegative groups leading to faster reactions.
  • It is noted that OH is a strong activating group for aromatic compounds, while NO2 is a strong deactivating group, affecting the speed of reactions involving these compounds.
  • In nucleophilic substitution, the stability of the leaving group is highlighted as a key factor, with OH being a poor leaving group compared to SO4H, which is considered an excellent leaving group.
  • A participant raises a question about the reactivity of compounds with both a hydroxyl group and a carboxylic acid group (e.g., OH-R-COOH) and how to explain their reactivity.
  • Another participant asks for clarification on which specific reaction is being referred to in the context of the discussion.

Areas of Agreement / Disagreement

Participants express differing views on the factors influencing reactivity, particularly regarding the effects of different functional groups in various types of reactions. The discussion remains unresolved as participants seek clarification and further explanation.

Contextual Notes

The discussion does not fully address the assumptions regarding the specific types of reactions being considered, nor does it resolve the implications of having multiple functional groups in a single compound.

Chuckj
Messages
6
Reaction score
0
There are several substanecs different only in a chemical group linked to the same opsition for all those substances. how can i know which one reacts fastest ?

ie , OH-R, ON_2-R, O_3P-R, O_4S-R...

Thanks
 
Chemistry news on Phys.org
Chuckj said:
There are several substanecs different only in a chemical group linked to the same opsition for all those substances. how can i know which one reacts fastest ?

OH-R, ON_2-R, O_3P-R, O_4S-R...

It depends what you are trying to do.

If it's aromatic substitution, more negative stuff connected to the aromatic makes a faster reaction. OH on a benzene ring is a very strong activating group, so phenol will react quickly. Same deal with aniline, NH2 is a strong activating group. NO2 on a benzene ring is a strong deactivating group (the oxygens make the nitrogen positive), so nitrobenzene is a slouch when it comes to reactions.

If it's nucleophilic substitution, the speed is determined by the stability of the leaving group. OH is a horrible leaving group, so that is a slow reaction. SO4H is an excellent leaving group, so that will leave quickly. Water is an even better leaving group, so using acid around oxygens makes stuff happen faster (true for both organic and inorganic).
 
Last edited:
Thank you very much,
But what if I have substances like

OH-R-COOH
O2N-R-COOH
O4P-R-COOH
...
how can i explain then ?
 
which reaction are you referring to?
 

Similar threads

Can you make pure water acidic by adding free protons to it?
  • · Replies 6 ·
Replies
6
Views
2K
Storing chemicals on my balcony (storing in changing temps)
  • · Replies 14 ·
Replies
14
Views
3K
Chemically regenerating my auto's catalytic converter?
  • · Replies 19 ·
Replies
19
Views
11K
Undergrad Dfns group action & group, written in terms of the other
  • · Replies 26 ·
Replies
26
Views
2K
Graduate Classification of reductive groups via root datum
  • · Replies 3 ·
Replies
3
Views
3K
Undergrad ##SU(2, \mathbb C)## parametrization using Euler angles
  • · Replies 15 ·
Replies
15
Views
4K
Undergrad Meaning of "passage to the quotient"?
  • · Replies 3 ·
Replies
3
Views
2K
Why Is Understanding Biochemistry Foundations Crucial for Medical Students?
  • · Replies 2 ·
Replies
2
Views
2K
Enantiomer / Diastereomer Chemical and Physical Properties
  • · Replies 3 ·
Replies
3
Views
23K
MHB Group R^× isomorphic to the group R?
  • · Replies 5 ·
Replies
5
Views
3K