Oxidation of alcohols confusion (H2Cro4 and HOCl)

[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?

 

[hypervalent_iodine]

It's perhaps not very well presented. There are chromium based reagents that are used to oxidise to the aldehyde and not continue to the acid (PCC and PDC). As far as primary alcohols go, sodium hypochlorite would be an alternative to reagents such as PCC or PDC, rather to those used to oxidise all the way to the acid. It is also a useful alternative for secondary alcohols.