Jones reagent versus PCC
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.
Let Transformation Tutoring help you ace your organic chemistry class and find passion and love for the subject. Our organic chemistry tutors in Brooklyn, NYC, and online are here to help you and talk to you. Please call 646-407-9078 and we will gladly discuss your needs.