# Reaction of secondary alcohol with ammoniacal silver nitrate (Tollens' reagent)

What are the products of the reaction of 2-butanol with silver nitrate?

For the moment, I am a bit stumped as I only have $\ce{AgNO3}$ as an oxidizing agent to form a carboxylic acid from an aldehyde. Additionally, the lack of $\ce{H2O}$ indicates that this is not the reaction I should be looking for. The only reaction that seems feasible to me is an SN2 mechanism where the nitrate anion acts a nucleophile and the hydroxide ion as the leaving group.

Here is my proposed mechanism much in the style of Tollen's reaction with an aldehyde.

• Do you know the product of the reaction? Or the reaction conditions, solvent? – Jori Apr 25 '15 at 21:04
• @Jori, No they only gave this information, but in our course we have only seen $\ce{AgNO3}$ as an oxidizing agent for aldehydes. I guess it would be safe to assume that the solvent was water but even then I am not sure how the reaction would proceed... – Matthieu Kratz Apr 26 '15 at 9:23
• @Matthieu Kratz Are you are referring to ammoniacal silver nitrate (Tollens' Reagent)? – bon Apr 26 '15 at 17:55
• @bon, yup referring to tollen's reagent, but the form in which were given it was a mix silver nitrate and ammonia/ water. I can think of a mechanism that would work on ketones, but I have never seen it used in such a way. – Matthieu Kratz Apr 26 '15 at 17:59
• Your question does not make complete sense. In the comments you clarified that it is ammoniacal silver nitrate, but then in the question image you had still only written $\ce{AgNO3}$. IIRC ammoniacal water is important for Tollen's reagent to function. Please clarify that the initial question image was incomplete, otherwise your question body and question title are currently mismatching. – Gaurang Tandon Mar 16 '18 at 5:30

This question refers to the use of Tollens' Reagent (ammoniacal silver nitrate). The oxidising species here is the diamminesilver(I) complex $\ce{[Ag(NH3)2]+}$.