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Jones reagent versus PCC

organic chemistry tutor NYC

In organic chemistry students will learn both Jones (CrO3/ aq H2SO4) and PCC reagents and will need to know how to differentiate between the two. Both reagents oxidize alcohols. Only secondary and primary alcohols can be oxidized, since oxidizing tertiary alcohol will lead to a carbon with five bonds which is impossible. Both Jones reagent and PCC turn a secondary alcohol into a ketone, going from C-OH to C=O. The difference comes to the primary alcohols. PCC turns a primary alcohol into an aldehyde (C-OH to C=O). However, Jones reagent is strong and oxidizes primary alcohol further to carboxylic acids (C-OH to COOH).

What other reagents produce C=O? Ozonolysis (O3/ H2O2 or DMS). Ozonolysis is done on alkenes. It can be under reductive and oxidative conditions. Under reductive conditions, O3/DMS, all we need to do is break the double bond and attach an O on each side. Therefore, reductive ozonolysis will create ketones and aldehydes. Ozonolysis under oxidative contusions, on the other hand, will lead to carboxylic acids instead of aldehydes.

DMP is the final reagent we will discuss here. DMP is used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. Therefore DMP is similar to PCC in the end results it gives.

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