Alcohol Oxidation Reactions (PCC, Jones Reagent)

Let’s say you want a ketone or aldehyde.  Alcohols can be oxidized to either.  

We can even go all the way up to carboxylic acids.
 

When you hear oxidize in your class, you probably discussed the oxidation state or loss of electrons.  To keep things simple, think of oxidation as making a double-bonded oxygen from a single-bonded oxygen.  

There are newer, cleaner techniques for oxidizing.  Chemists are moving away from Swern oxidations because the byproduct just smells awful.  PCC and Jones reagent are classic examples, but are highly carcinogenic due to the chromium VI contained within each.  

Newer techniques such as TPAP NMO (pronounced T-PAP N-M-O) and TEMPO (like in music) Bleach are used in wet labs.

You probably don’t care because the test is on chromium VI oxidations, so let’s focus on PCC and Jones Reagent.

Jones can take primary alcohols to carboxylic acids or secondary alcohols to ketones.

Think for a moment why tertiary alcohols won’t oxidize.

Jones oxidation is done normally in the presence of sulfuric acid.
 

PCC can be done in organic solvent such as DCM and PCC produces the same product as Jones except for one key difference.  Primary alcohols are oxidized to aldehydes.  It stops there; primary alcohols do NOT go to carboxylic acids.