Reduction of Acyl Halides

[CedarZ4]

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Hey guys, I have a question about acyl halides.

If we have an acid chloride (RCOCl) and react it with NaBH4, what will the product be? Will we get an alcohol (RCHOHCl) or will we get an aldehyde (RCOH). Is that even an alcohol (RCHOHCl)? Or does the Cl leaves as well and you just get (RCH2OH).

I know that NaBH4 reduces carbonyl to alcohols (usually) but for some reason, I just keeping thinking the Cl is supposed to leave first before reducing the O.

When reacting Acid Chloride with NaBH4, will we get an alcohol or an aldehyde? What about if we used LAH?

Thanks

 

[dent4]

From what I've been taught, I'm pretty sure NaBH4 reduces just aldehydes and ketones whereas LiAlH4 reduces esters, nitriles, acids, ketones, or aldehydes. Idk about that question tho? I personally think it wouldn't reduce for the simple fact that it has to be an aldehyde or ketone, but i'm not a 100% sure.

 

[NDPitch]

According to chads vids, an acyl halide can reduce to an alcohol because Cl is a good leaving group. So you'd have...

RCOCl + NaBH4 ---> ---> R-C-OH