Hydration reaction

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and 2-butanol.

Organic chemistry

Epoxides to glycol

Several billion kilograms of ethylene glycol is produced annually by the hydration of ethylene oxide:

Acid catalysts are typically used.

Alkenes

For the hydration of alkenes, the general chemical equation of the reaction is the following:

A hydroxyl group (OH⁻) attaches to one carbon of the double bond, and a proton (H⁺) adds to the other carbon of the double bond. The reaction is highly exothermic. In the first step, the alkene acts as a nucleophile and attacks the proton, following Markovnikov's rule. In the second step an H₂O molecule bonds to the other, more highly substituted carbon. The oxygen atom at this point has three bonds and carries a positive charge (i.e., the molecule is an oxonium). Another water molecule comes along and takes up the extra proton. This reaction tends to yield many undesirable side products, (for example diethyl ether in the process of creating Ethanol) and in its simple form described here is not considered very useful for the production of alcohol.