destroyer roadmap question

[topdent1]

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My question is about the reaction of ethyl benzene with K2Cr2O7. There is a carbon missing int the products?!?!? The result is benzoic acid. Is this an error?

 

[whoaaitzkyle]

My question is about the reaction of ethyl benzene with K2Cr2O7. There is a carbon missing int the products?!?!? The result is benzoic acid. Is this an error?

K2Cr2O7 is a really strong oxidizing agent. It will change that carbon chain into a carboxylic acid. Benzoic acid is the correct answer...good eye though!

 

[topdent1]

K2Cr2O7 is a really strong oxidizing agent. It will change that carbon chain into a carboxylic acid. Benzoic acid is the correct answer...good eye though!

but where did the extra carbon go?

 

[topdent1]

I really need to know the answer to this!

 

[excusezmoi]

which roadmap is this #?

 

[bigasianpianist]

Well the potassium dichromate oxidizes any alkyl group on the aromatic ring, and it leaves it with only a carboxylic acid. The rest of the alkyl becomes another molecule in the solution. I'd do the mechanism but all you have to know is that the strong oxidizers (i.e. the K2Cr2O7, KMnO4 and etc) will remove the rest of the alkyl and leave a COOH in its place. Hope this helps

 

[topdent1]

Well the potassium dichromate oxidizes any alkyl group on the aromatic ring, and it leaves it with only a carboxylic acid. The rest of the alkyl becomes another molecule in the solution. I'd do the mechanism but all you have to know is that the strong oxidizers (i.e. the K2Cr2O7, KMnO4 and etc) will remove the rest of the alkyl and leave a COOH in its place. Hope this helps

So even if it was a 10 carbon chain, it would screw the 9 carbons and convert that one into an acid? Thanks!

 

[bigasianpianist]

Darn tootin. gL