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Organic Chemistry Text Book (CHEM 3401 and 3402)

12.1 Alcohol Structure

In the alcohol functional group, a carbon is single-bonded to an OH group (the OH group, by itself, is referred to as a hydroxyl). Except for methanol, all alcohols can be classified as primary, secondary, or tertiary. In a primary alcohol, the carbon bonded to the OH group is also bonded to only one other carbon. In a secondary alcohol and tertiary alcohol, the carbon is bonded to two or three other carbons, respectively. When the hydroxyl group is directly attached to an aromatic ring, the resulting group is called a phenol. The sulfur analog of an alcohol is called a thiol (from the Greek thio, for sulfur).

Note that the definition of a phenol states that the hydroxyl oxygen must be directly attached to one of the carbons of the aromatic ring. The compound below, therefore, is not a phenol - it is a primary alcohol.

The distinction is important, because as we will see later, there is a significant difference in the reactivity of alcohols and phenols.

The deprotonated forms of alcohols, phenols, and thiols are called alkoxidesphenolates, and thiolates, respectively. A protonated alcohol is an oxonium ion.