0
$\begingroup$

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

$\endgroup$
  • $\begingroup$ 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
1
$\begingroup$

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.

| improve this answer | |
$\endgroup$
1
$\begingroup$

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.

| improve this answer | |
$\endgroup$

Not the answer you're looking for? Browse other questions tagged or ask your own question.