Deuterium Exchange

Due to the acidic nature of α hydrogens they can be exchanged with deuterium by reaction with D₂O (heavy water). The process is accelerated by the addition of an acid or base; an excess of D₂O is required. The end result is the complete exchange of all α hydrogens with deuterium. 

General reaction

 

Example 1: Deuterium Exchange

Mechanism in basic conditions

1) Enolate Formation

 

2) Deuteration

Problems

1)  Please draw the product for the following reactions.

2) Answers

Contributors

• Prof. Steven Farmer (Sonoma State University)