When the following compound is hydrated in the presence of...

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Key Concepts

Carbocation Intermediate Reversibility

Often in acid-catalyzed reactions, the formation of a carbocation occurs reversibly, meaning that protonation and deprotonation can interconvert the alkene and the intermediate. However, if the unreacted starting material retains its isotopic labels, it suggests that the reversible exchange at the site of protonation (or deuteration) is not occurring, indicating that the step is either irreversible or proceeds without scrambling isotopic labels.

Acid?Catalyzed Hydration Mechanism

This mechanism involves the protonation of an alkene to form a carbocation intermediate, followed by the attack of water and subsequent deprotonation to yield an alcohol. It is an electrophilic addition process where the initial step determines much of the reaction’s course.

Isotopic Labeling with Deuterium

Using deuterium as a tracer allows chemists to track atom movements during a reaction. The retention of deuterium in the unreacted alkene implies that there is no significant H/D exchange during the reaction, providing insight into the reaction pathway and indicating that the protonation step does not lead to deuterium scrambling.

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