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Organic Chemistry Text Book (CHEM 3401 and 3402)

12.6 Reactions of Alcohols and Phenols

The functional group of the alcohols is the hydroxyl group, –OH. Unlike the alkyl halides, this group has two reactive covalent bonds, the C–O bond and the O–H bond. The electronegativity of oxygen is substantially greater than that of carbon and hydrogen. Consequently, the covalent bonds of this functional group are polarized so that oxygen is electron rich and both carbon and hydrogen are electrophilic, as shown in the drawing on the right. Indeed, the dipolar nature of the O–H bond is such that alcohols are much stronger acids than alkanes (by roughly 1030 times), and nearly that much stronger than ethers (oxygen substituted alkanes that do not have an O–H group). The most reactive site in an alcohol molecule is the hydroxyl group, despite the fact that the O–H bond strength is significantly greater than that of the C–C, C–H and C–O bonds, demonstrating again the difference between thermodynamic and chemical stability. 

For a discussion of how acidity is influenced by molecular structure Click Here.