Is Acetaldehyde a Good Nucleophile for Aromatic Substitution?

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SUMMARY

Acetaldehyde is not a strong nucleophile for aromatic nucleophilic substitution due to its electron-withdrawing nature. The discussion highlights the challenges of using acetaldehyde in reactions with non-activated aromatic compounds. Participants emphasize the importance of the aromatic system's electron density and suggest that preserving the aldehyde functionality may complicate the substitution process. pKa data for acetaldehyde is also requested to better understand its reactivity in this context.

PREREQUISITES
  • Understanding of aromatic nucleophilic substitution mechanisms
  • Knowledge of pKa values and their relevance to nucleophilicity
  • Familiarity with electron-rich and electron-poor aromatic systems
  • Basic concepts of aldehyde reactivity in organic chemistry
NEXT STEPS
  • Research the mechanisms of aromatic nucleophilic substitution in detail
  • Investigate pKa values of acetaldehyde and other aldehydes
  • Explore strategies for enhancing nucleophilicity in aromatic systems
  • Study the effects of substituents on the reactivity of aromatic compounds
USEFUL FOR

Chemists, organic synthesis researchers, and students studying nucleophilic reactions in aromatic compounds will benefit from this discussion.

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?
 
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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