[frankenstein18]

My book (essential organic chemistry by paula yurkanis bruice 3rd edition) says that primary alcohols oxidize into aldehydes and that the oxidation contiues to form a carboxylic acid.

Then I'm given an example of this with H2CrO4 as the reducing agent

Then I'm told that since H2CrO4 is toxic HOCl is used instead. THn I'm given an example of this ( same primary alcohol used in the reduction with H2CrO4) BUT this time the primary alcohol doesn't keep oxidizing into a carboxylic acid!

Is it supposed to keep oxidizing and the book just assumes I think that or with HOCl do primary acids not keep oxidizing?

[kriggy]

It could be that H₂CrO₄ is stronger oxidation agent that NaOCl

[beardy]

James @ MOC gives a good explanation of alcohol oxidation levels.

http://www.masterorganicchemistry.com/2015/05/06/alcohol-oxidation-strong-and-weak-oxidants/

[orgopete]

Aldehydes are relatively easy to oxidize to carboxylic acids. Hypochlorous acid will not stop at an aldehyde. The reagents that stop at an aldehyde do so under anhydrous conditions. Water adds to aldehydes to form the hydrate. The hydrate oxidizes just like any secondary alcohol except the product is a carboxylic acid.