Nucleophiles and carbonyl compounds .

  • Thread starter metalInferno
  • Start date
  • Tags
    Compounds
In summary, bases such as OH- preferentially abstract alpha-hydrogen from carbonyl compounds like ketones and aldehydes, while amines and their derivatives attack the carbon center of the carbonyl group through nucleophilic addition. The difference in reactivity is due to the stability of the intermediate species formed - in the case of hydroxide addition, a stable oxyanion is formed, while in the case of alpha-hydrogen abstraction, a more stable anion is formed. In aprotic solvents, nucleophilic addition is the only option, while in protic solvents, the intermediate species can pick up a proton and become stable alcohols. Additionally, amines preferentially form
  • #1
metalInferno
35
0

Homework Statement


Why do bases like OH- etc. remove [tex]\alpha-H[/tex] from carbonyl compounds like ketones and aldehydes (aldol condensation) whereas amines and derivatives like [tex]NH_{3}[/tex]attack the carbon centre of carbonyl groups ?

Homework Equations



none.

The Attempt at a Solution



Thought of all possible reasons but am still confused .
 
Physics news on Phys.org
  • #2
Many good nucleophiles are not strong enough bases to abstract protons from ketones and aldehydes. The only game in town is nucleophilic addition. Is an amine a strong enough base to deprotonate a proton alpha to a carbonyl?

In the case of hydroxide addition to a carbonyl, you have an oxyanion intermediate that is not delocalized... it is pretty much localized on the oxygen. The structure resembles an alkoxide. Stable? In a protic solvent it will pretty rapidly pick up a proton and become the geminal diol. Are geminal diols stable? In the case of alpha hydrogen abstraction, the anion is delocalized over both the oxygen and the alpha (or beta) anion. That is a more stable intermediate.

In a nucleophilic addition, the intermediate localizes the negative charge on the oxygen but it can pick up a proton from solvent and form an alcohol. Pretty stable.

In an aprotic solvent what happens?
 
  • #3
ok ... i am getting some of it . Let us take a base like [tex]NH^{-}_{2}[/tex] . This is a very good base . But as far as i know , this does not abstract the hydrogen , but attacks the carbon center to form amides .
 
  • #4
One more question , how come [tex]NH^{-}_{2}[/tex] forms amides with acid derivatives and not with aldehydes . This might help in understanding .
 

What are nucleophiles?

Nucleophiles are molecules or ions that have a tendency to donate an electron pair to form a covalent bond with an electrophile. They are electron-rich and are attracted to positively charged atoms or functional groups.

What are carbonyl compounds?

Carbonyl compounds are organic compounds that contain a carbon-oxygen double bond, also known as a carbonyl group. They can be either aldehydes or ketones, depending on where the carbonyl group is located in the molecule.

How do nucleophiles react with carbonyl compounds?

Nucleophiles can react with carbonyl compounds through nucleophilic addition, where the nucleophile attacks the electrophilic carbon atom of the carbonyl group, breaking the double bond and forming a new bond with the nucleophile. This results in the formation of a tetrahedral intermediate, which can then undergo further reactions.

What factors influence the reactivity of nucleophiles towards carbonyl compounds?

The reactivity of nucleophiles towards carbonyl compounds is influenced by several factors, including the strength of the nucleophile, the electronic and steric effects of the nucleophile, and the nature of the carbonyl compound itself. For example, more electronegative and basic nucleophiles tend to be more reactive, while bulky nucleophiles may have steric hindrance and be less reactive.

What are some examples of nucleophiles and carbonyl compounds?

Some common nucleophiles include oxygen and nitrogen-containing compounds such as water, alcohols, amines, and carboxylic acids. Examples of carbonyl compounds include formaldehyde, acetone, and aldehydes and ketones found in sugars, fats, and proteins.

Similar threads

  • Biology and Chemistry Homework Help
Replies
2
Views
1K
  • Biology and Chemistry Homework Help
Replies
14
Views
3K
Replies
1
Views
1K
  • Biology and Chemistry Homework Help
Replies
4
Views
1K
  • Biology and Chemistry Homework Help
Replies
1
Views
2K
  • Biology and Chemistry Homework Help
Replies
28
Views
4K
  • Biology and Chemistry Homework Help
Replies
14
Views
3K
  • Biology and Chemistry Homework Help
Replies
4
Views
4K
  • Biology and Chemistry Homework Help
Replies
11
Views
6K
  • Biology and Chemistry Homework Help
Replies
9
Views
3K
Back
Top