[noodlesoup]

hi guys,
i've been working on my lab and got stuck for the reaction mechanism for nitric acid and acetic andydride. i attempted to draw the mechanism below but not sure where to proceed after that. Can you give me a suggestion for this mechanism. Thanks alot.
Also, by any chance, did anyone work on lab involve Dinitration before?  what is it exactly? thanks

[nj_bartel]

I just started this material, so I'm sure I'll get corrected if I'm wrong, but anyway -

I think the carbonyl oxygen is the most basic site, and as thus it should be the oxygen that gets protonated.  That would make the carbonyl carbon more electrophilic, and from there you could do a substitution, but I'm not sure how the nitrate ion acts as a nucleophile - it looks pretty awful to me.

[noodlesoup]

but then how can you get the acetate and carboxylic acid as the products though...it doesn't make sense to me    i know these two products are coming out from the acetic anhydride but not sure how the pathway goes

[ROBINSON]

In a study of the action of a mixture of 70% nitric acid and acetic anhydride on alkenes and anisole Bordwell
and Garbish  suggested that the nitrating mixture contains protonized acetyl nitrate molecules which have a more
powerful nitrating action than molecules of acetyi nitrate itself.read the article attached also...

[orgopete]

I won't destroy your fun, but if acetic anhydride and nitric acid give acetate anion, acetic acid, and nitrate anion (not shown), then you will have taken two neutral compounds and prepared two anions from it. I suggest writing out every bond making and breaking steps carefully. You can then discover a correct mechanism.