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


1 Answer 1


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.

  • 2
    $\begingroup$ answered here chemistry.stackexchange.com/questions/94620/… $\endgroup$
    – Waylander
    May 28, 2018 at 18:00
  • $\begingroup$ I have no access to a drawing package $\endgroup$
    – Waylander
    May 28, 2018 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, 2018 at 17:37

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.