Sciencemadness Discussion Board - Hydrolysis of alkyl halides

Hydrolysis of alkyl halides

Monoamine - 1-12-2022 at 04:48

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

clearly_not_atara - 1-12-2022 at 06:36

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

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

CharlieA - 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).

DraconicAcid - 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.

Dr.Bob - 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.