Is Acetaldehyde a Good Nucleophile for Aromatic Substitution?

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Acetaldehyde's behavior as a nucleophile in aromatic nucleophilic substitution is under discussion, particularly regarding its effectiveness in inserting into an aromatic compound. The conversation highlights the importance of the aromatic system's electron density, noting that if the aromatic group is not electron-rich, the reaction may be challenging. There is also a focus on whether the aldehyde functionality needs to be preserved in the final product, indicating that the reaction conditions and mechanisms may need careful consideration to achieve the desired outcome. Participants are seeking pKa data to better understand the reactivity of acetaldehyde in this context.
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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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