Can you help me get my oxidants straight?

[NumbaOneStunna]

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I know that for example only primary alcohols can go to carboxy acids and stuff like that. But I have a hard time remembering what all of the different oxidizing agents are and whether or not they are strong (taking alcohols to carboxy acids if enough H's) or mild (taking it to an aldehyde) or can do funky things like oxidizing a alkylbenzene to a carboxylic acid while getting of all of the alkane's carbons except the one for the carboxy acid.

So can someone break this down for me please?

Thanks,
NumbaOneStunna
(annoyed that his orgo class used different reagents to do the same thing)

 

[vlct0ria]

I know that for example only primary alcohols can go to carboxy acids and stuff like that. But I have a hard time remembering what all of the different oxidizing agents are and whether or not they are strong (taking alcohols to carboxy acids if enough H's) or mild (taking it to an aldehyde) or can do funky things like oxidizing a alkylbenzene to a carboxylic acid while getting of all of the alkane's carbons except the one for the carboxy acid.

So can someone break this down for me please?

Thanks,
NumbaOneStunna
(annoyed that his orgo class used different reagents to do the same thing)

Mild oxidants- PCC/PDC
Strong oxidants- KMnO4, Jones reagent, Na2Cr2O7, K2Cr2O7

KMnO4 also oxidizes alkylbenzenes to benzoic acids, and also can oxidize alkenes. That's not everything, but that can help you start a list. 🙂

 

[NumbaOneStunna]

Here's another one:
HIO4 cuts Vic Diols and mild oxidizes only those O's.

 

[SupahShyGuy]

Another obscure oxidizer is OsO4 (osmium tetraoxide) treated after with sodium bisulfite oxidizes across a double bond to give vic-diols via syn addition.

If a reagent has multiple Oxygens; it is an oxidizing agent. Also, think of oxidizing as creating more bonds to oxygens! (example: [LEAST OXIDIZED] Alkane = 0 bonds, alcohol = 1 bond, ketone/aldehyde = 2 bonds, carboxylic acids = 3 bonds! [most oxidized])

happy studying!