I can't seem to find much information on this topic but how does aluminium amalgam work as a reducing agent?
Could it be used to deoxygenate a carboxylic acid or amino acid to the corresponding alcohol or alkane?
If not , why not?
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$\begingroup$ Joel, in one place you are saying that you are "Looking for an answer drawing from credible and/or official sources" and in another place "Please don't post any links". Please explain what citation format you would like the references to official sources to be in if you don't like links. Do you want patent numbers, journal volume and page, what are looking for? $\endgroup$– DavePhDOct 28, 2015 at 12:31
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$\begingroup$ I just mean an answer from someone that is credible/official so it's an original answer and they can explain it without a need for links . I mean no disrespect and fully appreciate your time , I'm not at all saying your not credible/official , I'm sorry if I worded it incorrectly. :) $\endgroup$– TechnetiumOct 28, 2015 at 12:34
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$\begingroup$ The chemistry theory behind why the amalgam reacts selectively as apposed to other reducing agents towards this style of compound is why the question is interesting. $\endgroup$– TechnetiumOct 28, 2015 at 12:48
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1$\begingroup$ Please see the help center, especially the entry on bounties. In short: They are non-refundable, i.e. you cannot get back your reputation points. You also cannot extend the period of the bounty. You can set a new bounty if you are not satisfied with the answers that have been given. You also might want to read the guide about flagging. $\endgroup$– Martin - マーチン ♦Nov 4, 2015 at 6:38
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1 Answer
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Could aluminium amalgam be used to deoxygenate a carboxylic acid or amino acid to the corresponding alcohol or alkane?
No. Aluminium amalgam has been used to selectively reduce other groups in molecules containing a carboxylic acid group, while preserving the carboxylic acid group.
See for example in Industrial Organic Nitrogen Compounds at page 139:
Some pyridine-carboxylic acids have been reduced to the corresponding dihydropyridine-carboxylic acids with aluminium amalgam.
See also the patent Polyene carboxylic acids and esters and manufacture thereof where aluminium amalgam is suggested as a mild reducing agent which preserves the carboxylic acid or ester group.
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$\begingroup$ So would it reduce an alcohol or a ketone to the alkane? $\endgroup$ Oct 28, 2015 at 11:10
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$\begingroup$ The first link you posted doesn't work with my phone unfortunately @DavePhD. Do you have a detailed example of a reaction mechanism so i can see how it used ( in theory!). $\endgroup$ Oct 28, 2015 at 11:17
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$\begingroup$ Also why does it act to protect the functional groups instead of deoxygenating all the functional groups. How is it selective and why won't it work? I can already find many examples of reactions it's used in. $\endgroup$ Oct 28, 2015 at 11:26
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$\begingroup$ Sorry @ DavePhD , just posting links and not providing the theory behind what's happening just isn't the answer I was looking for. I appreciate your help tho :) $\endgroup$ Oct 28, 2015 at 11:29
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1$\begingroup$ @Joel as far as I know, aluminum amalgam can be used to reduce a ketone to an alcohol, and zinc amalgam with HCL can be used to reduce some ketones to alkanes (Clemmensen reduction). But I'm not aware of aluminum amalgam being used in the same way. Maybe the HCl would react with the aluminum instead to form hydrogen gas, but I'm just guessing. Sorry if I didn't give you the info you were hoping for. $\endgroup$– DavePhDNov 2, 2015 at 12:53