Alkoxide Definition in Chemistry

An alkoxide is an organic functional group formed when a hydrogen atom is removed from a hydroxyl group of alcohol when reacted with a metal. It is the conjugate base of alcohol.

Alkoxides have the formula RO^- where R is the organic substituent from the alcohol. Alkoxides are strong bases and good ligands (when R is relatively small). Generally, alkoxides are unstable in protic solvents, but they do occur as reaction intermediates. Transition metal alkoxides are used as catalysts and to prepare coatings.

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Alkoxy Group Definition in Chemistry

By Anne Marie Helmenstine, Ph.D.

Example

Sodium reacting with methanol (CH₃OH) reacts to form the alkoxide sodium methoxide (CH₃NaO).

Preparation

There are several reactions to alcohol that produce alkoxides. They may be made by reacting an alcohol with a reducing metal (e.g., any of the alkali metals), by reaction with an electrophilic chloride (e.g., titanium tetrachloride), using electrochemistry, or via a metathesis reaction between a sodium alkoxide and a metal chloride.

Alkoxide Key Takeaways

• An alkoxide is the conjugate base of an acid.
• In a chemical reaction, an alkoxide is written as RO^-, where R is the organic group.
• An alkoxide is a type of strong base.

Sources

• Boyd, Robert Neilson; Morrison, Robert Thornton (1992). Organic Chemistry (6th ed.). Englewood Cliffs, N.J.: Prentice Hall. pp. 241–242. ISBN 9780136436690.
• Bradley, Don C.; Mehrotra, Ram C.; Rothwell, Ian P.; Singh, A. (2001). Alkoxo and Aryloxo Derivatives of Metals. San Diego: Academic Press. ISBN 978-0-08-048832-5.
• Turova, Nataliya Y.; Turevskaya, Evgeniya P.; Kessler, Vadim G.; Yanovskaya, Maria I. (2002). The Chemistry of Metal Alkoxides. Dordrecht: Kluwer Academic Publishers. ISBN 9780792375210.
• Williamson, Alexander (1850). "Theory of Ætherification". Phil. Mag. 37 (251): 350–356. doi:10.1080/14786445008646627