According to my chemistry teacher, sodium in ethanol can reduce ketones, aldehydes, acid halides, esters, cyanides, isocyanides, nitro compounds and acid anhydrides.

Now surfing over the web, I could only verify that it reduces, aldehydes, ketones and esters. Can someone please confirm whether Na in EtOH reduces other mentioned compounds also?

  • 1
    $\begingroup$ If it opens an ester, and anhydride should be pushover. I would say of all those you mention esters and ketones are the most inert. $\endgroup$
    – Karl
    Apr 17, 2020 at 12:22

1 Answer 1


$\ce{Na + ROH}$ reduces:

  1. Aldehydes to primary alcohol

  2. Ketones to secondary alcohol

  3. Esters ($\ce{RCOOR'}$) to mixture of two alcohols ($\ce{RCH2OH + R'OH}$)

  4. Cyanides to primary amine

  5. Isocyanides to secondary amine

  6. Alkyl nitro to primary amine

  7. Aryl nitro to aryl amine, can $\ce{LiAlH4}$ do same?

Couldn't verify for Acid anhydrides and for acid halides, but my instinct says it must reduce acyl halides and anhydrides too. As @Waylander states "anhydrides and acyl halides are likely to be converted to ethyl esters by the EtOH solvent and then reduced."

  • 5
    $\begingroup$ Anhydrides and acyl halides are likely to be converted to ethyl esters by the EtOH solvent and then reduced. $\endgroup$
    – Waylander
    Apr 17, 2020 at 12:49
  • $\begingroup$ @Waylander if you find any scholarly article for same, I request you to add that in my answer $\endgroup$
    – Zenix
    Apr 17, 2020 at 13:48
  • $\begingroup$ Thanks alot @Zenix and , I think you both are right, because both acid halides and anhydrides easily get converted into ethyl esters, which is more stable and less reactive so that part logically follows, cant understand how I couldnt make the connection $\endgroup$
    – arnav009
    Apr 17, 2020 at 15:30
  • $\begingroup$ @Zenix can you please provide any reference regarding cyanides , isocyanides and nitroalkanes $\endgroup$
    – arnav009
    Apr 17, 2020 at 15:32
  • $\begingroup$ @Zenix as far as i distinctly remember Aryl nitros get converted into azo compounds when treated with LiAlH4, i can confirm this since i have attempted many questions relating to this reactions from reputed books and JEE Advanced papers, if high concentration of nitrobenzene is kept with LiAlH4 it forms azo benzene $\endgroup$
    – arnav009
    Apr 17, 2020 at 15:35

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