quick question about Jones Reagent

[rah08e]

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I know that jones reagent reacts with an -R group of a benzene ring and turn it into a carboxylic acid, but why doesn't this work the same way with a straight chain such as 3-methyl-pentanol, where only the -OH is oxidized into the carboxylic acid?

Also, referring to the first part of the question, can the -R group on benzene be anything more complex than a straight alkyl chain?

-Thanks

 

[rpatel8]

I think the only requirement is that you have a benzylic hydrogen but I am not 100% sure.

 

[Hope30]

lol, when I read your post. I thought I saw Ronald Reagan. I believe from your statement, jones reagent is a strong oxidizing reagent and therefore would oxidize -OH for instance to -COOH or -R to -COOH. Not 100% sure, but logically make sense.

 

[adianadiadi]

The alkyl groups on benzene ring are oxidized to -COOH groups when treated with KMnO4 or K2Cr2O7. The benzene ring withdraws electrons from the alkyl groups and thus by facilitating the oxidation via aldehyde. See the Etard reaction at:
http://en.wikipedia.org/wiki/Étard_reaction

And compare the mechanism with that of jones reagent at: http://www.adichemistry.com/organic/organicreagents/jones/jones-reagent-reaction-1.html

Adi

 

[LetsGo2DSchool]

lol, when I read your post. I thought I saw Ronald Reagan. I believe from your statement, jones reagent is a strong oxidizing reagent and therefore would oxidize -OH for instance to -COOH or -R to -COOH. Not 100% sure, but logically make sense.

Ronald Reagen lol. He indeed was a character.