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

Tollens' reagent is usually used as a test for aldehydes, with which it gives a characteristic silver mirror: 



It is often said that Tollens' reagent does not react with alcohols. However, from personal experience, gentle heating of a primary alcohol with Tollens' will cause a small amount of oxidation and result in a fine black precipitate. Again, in my experience, secondary alcohols (such as in the question) do not react with Tollens' reagent and so I would predict that no reaction will take place here.

EDIT: Your proposed mechanism certainly looks plausible but whether it will take place in reality I can't say for certain (my experience of Tollens' reagent says no).