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Chemistry LibreTexts

Substitution of the Hydroxyl Hydrogen

As with the alcohols, the phenolic hydroxyl hydrogen is rather easily replaced by other substituents. For example, phenol reacts easily with acetic anhydride to give phenyl acetate. Likewise, the phenolate anion is an effective nucleophile in SN2 reactions, as in the second example below.

Examples:

RXN1.jpg

RXN2.jpg

Contributors

Prof. Steven Farmer (Sonoma State University)

William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry