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Reaction of secondary alcohol with ammoniacal silver nitrate (Tollens' reagent)
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Pamela Wallace
Reaction of secondary alcohol with ammoniacal silver nitrate (Tollens' reagent)
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).
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 anyway, but I wouldnt be suprised if one of the examiners made a mistake when writing the question because our chemistry deparment aint always the best...More
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.More
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).
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).
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