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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.

enter image description here

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  • $\begingroup$ Do you know the product of the reaction? Or the reaction conditions, solvent? $\endgroup$
    – Jori
    Apr 25, 2015 at 21:04
  • $\begingroup$ @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... $\endgroup$
    – Matthieu Kratz
    Apr 26, 2015 at 9:23
  • $\begingroup$ @Matthieu Kratz Are you are referring to ammoniacal silver nitrate (Tollens' Reagent)? $\endgroup$
    – bon
    Apr 26, 2015 at 17:55
  • $\begingroup$ @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. $\endgroup$
    – Matthieu Kratz
    Apr 26, 2015 at 17:59
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    $\begingroup$ 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. $\endgroup$
    – Gaurang Tandon
    Mar 16, 2018 at 5:30

1 Answer 1

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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:

enter image description here

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).

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  • $\begingroup$ 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. $\endgroup$
    – Matthieu Kratz
    Apr 26, 2015 at 18:51
  • $\begingroup$ 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. $\endgroup$
    – bon
    Apr 26, 2015 at 19:20
  • $\begingroup$ 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... $\endgroup$
    – Matthieu Kratz
    Apr 26, 2015 at 19:22

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