Oxidation States of Alcohols and Related Functional Groups

Oxidation States of Alcohols and Related Functional Groups 

Oxidation of alcohols leads to ketones, aldehydes, and carboxylic acids. These functional groups, in turn, undergo a wide variety of additional reactions. For these reasons, alcohol oxidations are some of the most common organic reactions. 

NEITHER addition or loss of H , H2O, HX, etc. is neither an oxidation nor a reduction. 

Oxidation states of alcohols. An alcohol is more oxidized than an alkane, yet less oxidized than carbonyl compounds such as ketones, aldehydes, and acids. Oxidation of a primary alcohol leads to an aldehyde, and further oxidation leads to an acid. Secondary alcohols are oxidized to ketones. Tertiary alcohols cannot be oxidized without breaking carbon-carbon bonds. 

We can tell that an oxidation or a reduction of an alcohol has taken place by counting the number of C—O bonds to the carbon atom. For example, in a primary alcohol, the carbinol (C—OH) carbon atom has one bond to oxygen in an aldehyde, the carbonyl carbon has two (more oxidized) and in an acid, it has three. Oxidation of an alcohol usually converts C—H bonds to C—O bonds. If we convert an alcohol to an alkane, the carbinol carbon loses its bond to oxygen and gains another bond to hydrogen. 

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Oxidation States of Alcohols and Related Functional Groups 467 11-2 Oxidation of Alcohols 469 11-3 Additional Methods for Oxidizing Alcohols 472 11-4 Biological Oxidation of Alcohols 474 11-5 Alcohols as Nucleophiles and Electrophiles Formation ofTosylates 476... 

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