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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

szentsas
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Archer
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1 Answers1

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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.

Nilay Ghosh
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Waylander
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    answered here https://chemistry.stackexchange.com/questions/94620/in-what-way-could-benzoin-give-tollens-test – Waylander May 28 '18 at 18:00
  • I have no access to a drawing package – Waylander May 28 '18 at 18:23
  • @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. – user55119 May 29 '18 at 17:37