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Chemistry LibreTexts

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

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