Is Acetaldehyde a Good Nucleophile for Aromatic Substitution?

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In summary, nucleophilicity of an aldehyde refers to its ability to attract and react with nucleophiles. It is determined by factors such as the presence of electron-withdrawing or electron-donating groups, steric hindrance, and solvent effects. Nucleophilicity and electrophilicity are inversely related, and a higher nucleophilicity leads to increased reactivity towards nucleophilic attacks. The nucleophilicity of an aldehyde can be altered by changing its electronic or steric environment, such as adding or removing electron-withdrawing or electron-donating groups.
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Deathcrush
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Does anyone know if an aldehyde, specifically, acetaldehyde behaves as a good nucleophile? I'm trying to insert an aldehyde in an aromatic compound through an aromatic nucleophilic substitution, any information or source to pKa data would also be appreciated, thanks!
 
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Are you trying to preserve the aldehyde functionality in your product? Are you trying to fomylate an aromatic group? Is the aromatic group electron rich?
 
  • #3
Yes, actually I want to do the molecule attached, as you can see, it is not an activated system, that's why I thought I could use aromatic nucleophilic substitution
 

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FAQ: Is Acetaldehyde a Good Nucleophile for Aromatic Substitution?

1. What is nucleophilicity of an aldehyde?

Nucleophilicity of an aldehyde refers to the ability of the aldehyde functional group (–CHO) to attract and react with a nucleophile, which is an electron-rich species.

2. How is nucleophilicity of an aldehyde determined?

The nucleophilicity of an aldehyde is determined by factors such as the presence of electron-withdrawing or electron-donating groups, steric hindrance, and solvent effects.

3. What is the relationship between nucleophilicity and electrophilicity of an aldehyde?

Nucleophilicity and electrophilicity are inversely related. As the nucleophilicity of an aldehyde increases, its electrophilicity decreases, and vice versa.

4. How does the nucleophilicity of an aldehyde affect its reactivity?

The higher the nucleophilicity of an aldehyde, the more reactive it is towards nucleophilic attacks. This is because a highly nucleophilic aldehyde is more likely to attract and react with a nucleophile.

5. Can the nucleophilicity of an aldehyde be altered?

Yes, the nucleophilicity of an aldehyde can be altered by changing its electronic or steric environment. For example, adding an electron-withdrawing group can decrease its nucleophilicity, while adding an electron-donating group can increase its nucleophilicity.

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