# 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... 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. 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. 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 $\ce{[Ag(NH3)2]+}$.

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).

• Thanks for answering, I guess they made a mistake in their question but could you check out the mechanism that I suggest in my post once I edit it, as the question seems to require a product. Apr 26 '15 at 18:51
• This is only based on my experience. I certainly don't profess to be an expert on the subject and so there might be some other reaction which I am not aware of.
– bon
Apr 26 '15 at 19:20
• Thanks for answering anyway, but I wouldn't be suprised if one of the examiners made a mistake when writing the question because our chemistry deparment ain't always the best... Apr 26 '15 at 19:22