Oxidation of Alcohols by PCC (Pyridinium chlorochromate)

PCC (Pyridinium chlorochromate) is a mild oxidizing agent used in organic chemistry. In this tutorial, we will study how different types of alcohols react differently with PCC and give products.



In this tutorial, we will discuss followings.

  1. Oxidation of primary, secondary alcohols by PCC
  2. Examples of primary alcohols oxidation to aldehyde
  3. Examples of secondary alcohols oxidation to aldehyde


Primary alcohols, secondary alcohols and tertiary alcohols with PCC

Only primary and secondary alcohols are oxidized to aldehydes and ketones respectively. Tertiary alcohols are not oxidized by PCC.

Primary alcohols, secondary alcohols and tertiary alcohols with PCC


Primary alcohol oxidation by PCC

Primary alcohols are oxidized to aldehydes by PCC. During the process, a water molecule is eliminated from the alcohol molecule. If strong oxidizing agents such as acidic potassium permanganate is used as an oxidizing agent, primary alcohol is oxidized to a carboxylic acid.

Primary alcohol oxidation by PCC

Oxidation of Ethanol by PCC reaction

Ethanol is oxidized to ethanal (acetaldehyde) by PCC. Oxidation state of the carbon atom (which is going to be oxidized), is changed from -1 to +1.

ethanol CH3CH2OH oxidation to ethanal CH3CHO by PCC


Propanol and PCC reaction

Propanol is oxidized to ethanoic acid (acetic acid) by PCC. Oxidation state of the carbon atom (which is going to be oxidized), is changed from -1 to +1.

propanol oxidation to propanal by PCC

Secondary alcohol oxidation by PCC

Secondary alcohols are oxidized to ketones by PCC. During the process, a water molecule is eliminated from the secondary alcohol molecule. If strong oxidizing agents such as acidic potassium permanganate is used as an oxidizing agent, primary alcohol is oxidized to a ketone.

secondary alcohol oxidation by PCC

2-propanol and PCC reaction

2-propanol is oxidized to propanone by PCC. Oxidation state of the carbon atom (which is going to be oxidized), is changed from 0 to +2.

2-propanol CH3CHOHCH3 oxidation to propanol by PCC

Why are tertiary alcohols not oxidized by PCC?

There are three C-C bonds around the carbon atom which has bonded with the -OH group. Therefore, there is no Hydrogen atom which has a joint with that carbon atom. Breaking those three C-C bonds is not easy because it needs a lot of energy. As PCC, strong oxidizing agents also cannot oxidize tertiary alcohols.



Questions



Is PCC a strong oxidizing agent

PCC is not a strong oxidizing agent. PCC is a mild oxidizing agent.



what does pcc do in a reaction

PCC is a mild oxidizing agent and used to oxidize primary and secondary alcohols to ketones or aldehydes.












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