Sunday, June 25, 2017

organic chemistry - 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.


enter image description here




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periodic trends - Comparing radii in lithium, beryllium, magnesium, aluminium and sodium ions

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