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Can someone help me find the mechanism for this reaction. I've been looking for it, but I haven't found it. Thank you.

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closed as off-topic by Philipp, G M, Klaus-Dieter Warzecha, Michiel, tschoppi Apr 10 '14 at 12:37

This question appears to be off-topic. The users who voted to close gave this specific reason:

If this question can be reworded to fit the rules in the help center, please edit the question.

  • $\begingroup$ Welcome to Chemistry.SE. I do not think this is a homework question, but a few people have voted to close your question because it violates the homework policy. Would you be willing to improve your question with some additional details, like what your thoughts are or where you have tried looking? $\endgroup$ – Ben Norris Apr 9 '14 at 10:21
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http://connection.ebscohost.com/c/articles/25511593/oxidation-nitric-acid-aliphatic-alcohols-diols-carboxylic-acids

http://pages.towson.edu/ladon/orgrxs/reagent/oxidizer.htm

It is a dangerous thing to do for the easy detonation of nitrate esters. Activated and stabilized alcohols, e.g., benzoin to benzil, are reasonable.

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The reaction starts with the formation of an organic nitric acid ester (as these compounds are dangerously unstable, as Uncle Al already pointed out, I would not recommend to use nitric acid for this oxidation). The negatively charged nitrate oxygen abstracts an alpha proton from the alkyl group, and $\ce{HNO2}$ is eliminated, yielding the aldehyde. Nucleophilic attack of nitrate on the carbonyl group and subsequent elimination of another equivalent $\ce{HNO2}$ finally yields the carboxylate.

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