ORGO: What does it mean when a molecule is 'quenched?'

In summary, quenching in organic chemistry refers to the process of terminating a chemical reaction and/or removing excess reactants through the addition of a specific reagent, such as water or acid. This is commonly done during the workup stage of a reaction.
  • #1
alphaj
17
0

Homework Statement



n/a

Homework Equations



n/a

The Attempt at a Solution


n/a

Just a question. I keep seeing that in SN2 reactions, sometimes a molecule is quenched by H2O or H3O. I've seen it turn an O- into an OH and also a heteroatom into an H. What exactly is going on here?
 
Physics news on Phys.org
  • #2
I found this on Wikipedia:

https://en.wikipedia.org/wiki/Quenching_(fluorescence)

Normally when I hear quench, I think of a samurai sword heated until it glows the color of the sun and is then thrust into to water to quench it ie cool it to room temperature. This process fixates the molecular structure of the metal. The faster-cooled metal is more flexible than the slower-cooled metal. Prior to heating, clay is applied to the sharp edge of the blade so that during quenching the sharp edge will cool more slowly and thus retain its sharpness and hardness.

http://www.pbs.org/wgbh/nova/samurai/swor-nf.html
 
  • #4
In this case, quenching means that you've essentially stopped the reaction. For example, say you're doing a Grignard reaction. The product that you get from addition of an organomagnesium halide to a carbonyl is an alkoxide. When you quench the reaction with water, the water will destroy all the Grignard reagents, halting the reaction, and the excess water will protonate the extremely basic alkoxide, giving a hydroxyl group.
 
  • Like
Likes jim mcnamara
  • #5
The term quench has many different meanings in chemistry from fluorescence quenching to reacting away excess reactant to terminate the chemical reaction. In the context of organic chemistry, the latter meaning is more common. It sounds like you are discussing the typical workup performed after a chemical reaction has completed:
https://en.wikipedia.org/wiki/Work-up_(chemistry)

See also this useful page discussing the practical aspects of setting up a reaction in organic chemistry, including the quenching and workup steps:
http://chem.chem.rochester.edu/~nvd/pages/reaction.php?page=roadmap
 

1. What is quenching in organic chemistry?

Quenching in organic chemistry refers to a process where a molecule is prevented from undergoing a chemical reaction by the addition of another compound. This can occur through various mechanisms, such as electron transfer or hydrogen bonding, and can result in the formation of a stable complex or the inhibition of a desired reaction.

2. How does quenching affect the reactivity of a molecule?

Quenching can significantly reduce the reactivity of a molecule by altering its electronic or steric properties. This can prevent the molecule from reacting with other compounds or participating in certain reactions, making it less reactive overall.

3. Why is quenching important in organic synthesis?

Quenching plays a crucial role in organic synthesis as it allows chemists to control and manipulate reactions. By selectively quenching certain molecules or functional groups, chemists can direct the course of a reaction and prevent unwanted side reactions from occurring.

4. Can quenching be reversed?

In some cases, quenching can be reversed by removing the quenching agent or using a different reaction condition. However, this is not always possible and the effects of quenching may be irreversible, leading to changes in the reactivity and properties of the molecule.

5. How can quenching be detected in a reaction?

Quenching can be detected through various analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy or mass spectrometry. These methods can reveal changes in the structure or properties of the molecule, indicating that quenching has occurred.

Similar threads

  • High Energy, Nuclear, Particle Physics
Replies
17
Views
2K
Replies
11
Views
2K
  • Biology and Chemistry Homework Help
Replies
1
Views
1K
  • Biology and Chemistry Homework Help
Replies
3
Views
1K
  • Biology and Chemistry Homework Help
Replies
1
Views
6K
  • Biology and Chemistry Homework Help
Replies
5
Views
2K
  • Biology and Chemistry Homework Help
Replies
2
Views
2K
  • Biology and Chemistry Homework Help
Replies
1
Views
5K
  • Biology and Chemistry Homework Help
Replies
1
Views
4K
  • Biology and Chemistry Homework Help
Replies
1
Views
2K
Back
Top