This is “The Formation of Carboxylic Acids”, section 15.3 from the book Introduction to Chemistry: General, Organic, and Biological (v. 1.0).
This book is licensed under a Creative Commons by-nc-sa 3.0 license. See the license for more details, but that basically means you can share this book as long as you credit the author (but see below), don't make money from it, and do make it available to everyone else under the same terms.
This content was accessible as of December 29, 2012, and it was downloaded then by Andy Schmitz in an effort to preserve the availability of this book.
Normally, the author and publisher would be credited here. However, the publisher has asked for the customary Creative Commons attribution to the original publisher, authors, title, and book URI to be removed. Additionally, per the publisher's request, their name has been removed in some passages. More information is available on this project's attribution page.
For more information on the source of this book, or why it is available for free, please see the project's home page. You can browse or download additional books there. You may also download a PDF copy of this book (72 MB) or just this chapter (4 MB), suitable for printing or most e-readers, or a .zip file containing this book's HTML files (for use in a web browser offline).
As we noted in Chapter 14 "Organic Compounds of Oxygen", the oxidation of aldehydes or primary alcohols forms carboxylic acids:
In the presence of an oxidizing agent, ethanol is oxidized to acetaldehyde, which is then oxidized to acetic acid.
This process also occurs in the liver, where enzymes catalyze the oxidation of ethanol to acetic acid.
Acetic acid can be further oxidized to carbon dioxide and water.
Caproic acid (hexanoic acid) can be prepared in an oxidation reaction from
Give the structures of the aldehyde and the carboxylic acid formed by the oxidation of isobutyl alcohol [(CH3)2CHCH2OH].
Caprylic acid (octanoic acid) can be prepared in an oxidation reaction from
Give the structures of the aldehyde and the carboxylic acid formed by the oxidation of 1,4-butanediol (HOCH2CH2CH2CH2OH).