I don't really understand the concept of organic oxidations.

  • Thread starter Thread starter LogicX
  • Start date Start date
  • Tags Tags
    Concept Organic
Click For Summary

Discussion Overview

The discussion centers around the concept of organic oxidations, particularly the understanding of electron transfer and oxidation states in organic compounds. Participants explore examples of organic oxidation reactions and seek clarification on how these processes differ from inorganic oxidations.

Discussion Character

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

Main Points Raised

  • One participant questions the concept of oxidation in organic chemistry, noting the lack of apparent electron transfer when hydrogen is replaced with oxygen.
  • Another participant suggests that replacing hydrogen with more electronegative groups around a carbon is considered oxidation, providing a ranking of oxidation states for various organic compounds.
  • A participant proposes assigning oxidation numbers to central carbon atoms as a method to understand oxidation states.
  • It is mentioned that the concept of oxidation states may be less useful in organic chemistry and can be seen as formalistic.
  • A specific example of glucose oxidation is provided, illustrating a reaction that involves the conversion of glucose to carbon dioxide and water.
  • One participant discusses the definition of oxidation in organic chemistry as the removal or addition of hydrogen, citing the oxidation of an alcohol to a ketone as an example.

Areas of Agreement / Disagreement

Participants express differing views on the applicability and understanding of oxidation in organic chemistry. There is no consensus on a singular definition or approach to organic oxidation, and the discussion remains unresolved regarding the clarity of electron transfer in these reactions.

Contextual Notes

Some participants note that the understanding of oxidation states may depend on specific definitions and that the examples provided may not fully capture the complexity of organic redox reactions.

LogicX
Messages
175
Reaction score
1
So let's say a hydrogen is replaced with an oxygen. Apparently this is an oxidation. But I just don't see any transfer of electrons going on. All the atoms still have the same number of valence electrons. Can someone give me an example of a simple organic oxidation and explain the electron transfer that is changing the oxidation states of the atoms? I can understand inorganic oxidations like Cr 3+ going to Cr 6+, I just can't wrap my mind around organic redox.
 
Chemistry news on Phys.org
If you change the groups around a carbon with more electronegative ones, that is considered oxidation in the organic sense.

Consider the following ranking from lowest oxidation state to largest:

CH4<CH3O<CH2O2<CO2

CH3S<CH3O

CH2O2(geminal diol)<CH2O2(formic acid) The geminal diol has two C-O bonds and the acid has 3.

CH3Cl<CH3F
 
chemisttree said:
CH4<CH3O<CH2O2<CO2

LogicX: try to assign oxidation numbers to central carbon atoms.
 
Borek has led you on the right track. Nevertheless I think your intuition is fine: The concept of oxidation states is much less usefull in organic chemistry and kind of formalistic.
 
For electron transfer in simple organic oxidation , look at the oxidation of glucose:
6O2 + C6H12O6 ----> 6CO2 + 6H2O
 
Yep! Total brain fart!

chemisttree said:
CH2(OH)2(geminal diol)<CH2O2(formic acid) The geminal diol has two C-O bonds and the acid has 3.
 
Last edited:
You better edit this formic acid :-p
 
Geez! One of those days.

Consider the following ranking from lowest oxidation state to largest:

CH4<CH3OH<CH2O2<CO2

CH3SH<CH3OH

CH2(OH)2(geminal diol)<CH2O2(formic acid) The geminal diol has two C-O bonds and the acid has 3.

CH3Cl<CH3F
 
In organic chemistry one definition of oxidation - reduction is the removel or addition
of hydrogen. For example the oxidation of an alcohol to a ketone.

C3H7OH + O ---> C3H6O + H2O
2 propanol ----- > propanone
 

Similar threads

  • · Replies 10 ·
Replies
10
Views
3K
Replies
3
Views
2K
Replies
4
Views
3K
  • · Replies 1 ·
Replies
1
Views
2K
  • · Replies 15 ·
Replies
15
Views
3K
  • · Replies 11 ·
Replies
11
Views
3K
  • · Replies 4 ·
Replies
4
Views
4K
Replies
2
Views
3K
Replies
5
Views
2K
  • · Replies 8 ·
Replies
8
Views
4K