PCC vs Jones Oxidation

Depending on whether you need to oxidize a primary alcohol to an aldehyde or a carboxylic acid, you can use either pyridinium chlorochromate (PCC) or Jones reagent (a solution of chromium trioxide, CrO3 in aqueous sulfuric acid):

 

 

Notice that the oxidation to carboxylic acids only happens when a primary alcohol is used. Secondary alcohols can only be oxidized to the corresponding ketone regardless of whether a strong or mild oxidizing agent is used.

Recall that carboxylic acids are higher up in the scale of oxidation states in organic chemistry; therefore, we can say that PCC is a mild oxidizing agent, while Jones is strong, as it oxidizes primary alcohols all the way to carboxylic acids:

 


Aside from PCC, there are a few other mild oxidizing agents such as pyridinium dichromate (PDC), Swern oxidation using DMSO, (COCl)₂ and Et₃N, and the Dess–Martin (DMP). Here is the list of the most common strong and mild oxidizing agents you will see in your organic chemistry class:

 

 

Check out this post for a comprehensive coverage of all the oxidizing agents with the corresponding mechanisms. The mechanism of Jones oxidation with CrO3 and H2CrO4 is also covered in this post

Practice

1.

Predict the major organic product when the following alcohol is treated with each oxidizing agent:

Answer

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Solution

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2.

Predict the major organic product for each of the following alcohol oxidation reactions:

 

a)
Answer

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b)
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c)
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d)
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e)
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f)
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g)
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h)
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i)
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j)
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