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Oxidation/Reduction

Emay
in Organic Chemistry

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Hello all,

 

I need to be able to write a complete mechanism for the oxidation of cyclohexanol, specifically using sodium dichromate dihydrate, and acetic acid. The problem is we were never given a complete mechanism in class so all I have are educated guesses. I wasn't able to find this particular reaction online(i found some with acetic acid, and some with Na2Cr2O7, but none with both) I'm pretty sure that the acetic acid protonate the oxidizing agent, and I'm sure it attatches to the ring and is then pulled off, but i'm not sure of the particulars.

 

I also wanted to know what was the most widely accepted mechanism for the reduction of cyclohexanone using NaBH4

As this sounds like homework, post what you think the mechanism is and I'll then give you some advice.

 

The sodium borohydride mechansim is very similar to that of lithium aluminium hydride with the major exception that the sodium does not coordinate to the carbonyl. See if you can work it out....I'll be happy to check any ideas you have

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