How would you oxidize aniline to nitrobenzene?

[FROGGBUSTER]

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Any way?

One more question.

Do Wolf-Kischner and Clemenson both completely reduce all aldehydes and ketones to alkanes?

 

[indigenoustw]

Any way?

From my notes, I think you can use potassium permanganate to oxidize it.

The other question...can't think of it on top of my mind yet lol (haven't been studying ochem yet)

 

[rockclock]

From my notes, I think you can use potassium permanganate to oxidize it.

The other question...can't think of it on top of my mind yet lol (haven't been studying ochem yet)

it's been a while, but i'm pretty sure that would give you a shi+load of products, only a tiny fraction of which would actually be nitrobenzene. you'd probably have just as much yield going back to benzene and nitrating back (including protecting/unprotecting steps if you have more to the molecule)

 

[Golfguy]

Question 1.

Yes, you could use HCrO4 to oxidize it. Or, you could add NaNO2 in acid to form the diazonium, then add H3PO4, then add HNO3 in Sulfuric.


Question 2.

Yes, they both will reduce aldehydes and ketones to the corresponding alkanes.🙂

 

[indigenoustw]

you'd probably have just as much yield going back to benzene and nitrating back (including protecting/unprotecting steps if you have more to the molecule)

You are probably right. It's not the traditional way I would do it as I recall this question before when i was taking ochem few years ago (I just looked for it from my notes, and it was written without any conditions associated with it lol bad note taking). But yea, starting from benzene would definitely give you a better yield by nitration.

 

[rockclock]

You are probably right. It's not the traditional way I would do it as I recall this question before when i was taking ochem few years ago (I just looked for it from my notes, and it was written without any conditions associated with it lol bad note taking). But yea, starting from benzene would definitely give you a better yield by nitration.

oh no doubt permanganate is fine for an answer on a test, one of the products is definitely going to be nitrobezene...but if i were in a lab trying for yield I wouldn't hit it hard with a strong oxidizer like that. i actually like golf's second method the best, again assuming that it works since it's been too long for me to be able to confirm

add NaNO2 in acid to form the diazonium, then add H3PO4, then add HNO3 in Sulfuric.

 

[FROGGBUSTER]

thanks guys.