Why does 3-hydroxy-butan-2-one give a positive Tollens' test despite the absence of an aldehyde group? What is the mechanism?

Sturcture of 3-hydroxy-butan-2-one


From the Wikipedia entry on Tollens 1

Tollens' reagent is a chemical reagent used to determine the presence of an aldehyde, aromatic aldehyde and alpha-hydroxy ketone functional groups

The substrate you have drawn is an alpha-hydroxy ketone.

  • 1
    $\begingroup$ Please add the mechanism $\endgroup$ – Archer May 28 '18 at 17:49
  • 2
    $\begingroup$ answered here chemistry.stackexchange.com/questions/94620/… $\endgroup$ – Waylander May 28 '18 at 18:00
  • $\begingroup$ Its very vastly presented in that answer, could you please add the specific mechanism here? $\endgroup$ – Archer May 28 '18 at 18:19
  • $\begingroup$ I have no access to a drawing package $\endgroup$ – Waylander May 28 '18 at 18:23
  • $\begingroup$ @Abcd: What do you mean by "very vastly presented" and " the specific mechanism" in regard to Waylander's link? Aldehydes are oxidized by Tollens' reagent. So are some other functionalities. A positive test MAY indicate the presence of an aldehyde. $\endgroup$ – user55119 May 29 '18 at 17:37

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