R3COH

R3COH denotes a class of tertiary alcohols in which the carbon bearing the hydroxyl group is attached to three carbon substituents. In this general representation, the central carbon carries an OH group and three R groups (R, R', and R''), so compounds in this class include tert-butyl alcohol and other tertiary alcohols. The simplest member is tert-butyl alcohol, also known as 2-methyl-2-propanol, with the formula (CH3)3C–OH.

Tertiary alcohols can be prepared by several routes. They arise from the acid-catalyzed hydration of alkenes in which the most substituted carbon bears the hydroxyl group, following Markovnikov addition. They can also be formed by the reaction of Grignard reagents with ketones, followed by aqueous workup, which converts the corresponding tetra-substituted alkoxide into a tertiary alcohol. Tertiary alcohols are generally stable to mild oxidation, because oxidation would require breaking a C–C bond at the tertiary center; however, strong oxidants can cleave C–C bonds and convert tertiary alcohols into carboxylic acids or other fragments.

Reactions of R3COH reflect the reactivity of a tertiary carbocation framework in many cases. They readily undergo dehydration under acidic conditions to yield alkenes, and they react with hydrogen halides to form tertiary alkyl halides via an SN1 mechanism. They are less prone to oxidation than primary or secondary alcohols and do not undergo simple oxidation to carbonyl compounds under ordinary conditions.

R3COH compounds are important as solvents, intermediates in organic synthesis, and precursors to various functionalized molecules. They require careful handling due to flammability and potential irritancy.