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Author: Subject: Hydrolysis of alkyl halides
Monoamine
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[*] posted on 1-12-2022 at 04:48
Hydrolysis of alkyl halides


Would NaBH4 or LiAlH4 reduce aliphatic halogens to H?

For instance would

CH3-(CH2)-(CH2)-(H2C-Cl) become (CH3)-(CH2)-(CH2)-(CH3) when treated with NaBH4

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clearly_not_atara
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[*] posted on 1-12-2022 at 06:36


This is not hydrolysis, it's called hydrogenolysis. But see:

https://pubs.acs.org/doi/10.1021/ja00959a028




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[*] posted on 1-12-2022 at 15:28


You can learn about this reaction just about anywhere. For example, in five minutes or so, I found references in Wikipedia, and several YouTube videos. Also, I can't imagine there is not a relatively current organic chemistry textbook that doesn't mention this reaction. Hydrolysis of alkyl halides generally refers to their reaction with wit water to produce alcohols (alkanols).
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[*] posted on 2-12-2022 at 14:52


If you want to turn an alkyl halide into an alkane, react it with magnesium to form a grignard and add water.



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[*] posted on 2-12-2022 at 17:32


That's certainly one of the simplest ways (Grignard), will work best for bromides, some chlorides work, but more challenging. But very cheap, simple, and straightforward, just need some dry ether or THF in order to initiate it, once started you can add wet ether to swap the MgX for the H.
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