Introduction
In chemistry, a hydration reaction refers to the process where a compound undergoes a transformation through the incorporation of water. More specifically, within organic chemistry, this involves the addition of water to an unsaturated compound, typically an alkene or alkyne. During this reaction, a hydroxyl group (OH) becomes attached to one of the carbon atoms involved in the double bond, while a proton (H+) connects to the adjacent carbon. This reaction releases a significant amount of energy, making it exothermic. Initially, the alkene serves as a nucleophile, targeting and bonding with a proton in accordance with Markovnikov’s rule. Subsequently, a water molecule forms a bond with the carbon atom that has a higher degree of substitution, resulting in an oxonium ion with a positively charged oxygen atom due to its three bonds. The process concludes when another water molecule interacts with the oxonium ion to remove the surplus proton. Notably, this reaction can lead to various unwanted byproducts, such as diethyl ether during ethanol production, rendering the basic version of this reaction somewhat inefficient for alcohol synthesis.
Reaction
Regioselectivity: Markovnikov
Stereospecificity: syn + anti
Intermediate: carbocation
Since a carbocation intermediate is formed, the reaction is also susceptible to carbocation rearrangements, as shown below:
Mechanism
Mechanism without carbocation rearrangement:
Mechanism with a carbocation rearrangement: