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Chemistry LibreTexts

Deuterium Exchange

  • Page ID
    1159
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    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

    Figure 1.jpg

    Example 1: Deuterium Exchange

    166152577467808613.png

    Mechanism in basic conditions

    Step 1: Enolate Formation

    Figure 3.jpg

    Step 2: Deuteration

    Figure 4.jpg

    Exercise \(\PageIndex{1}\)

    Please draw the product for the following reactions.

    imageedit_11_3636572242.png

    Answer

    imageedit_13_6945014442.png


    Deuterium Exchange is shared under a CC BY 4.0 license and was authored, remixed, and/or curated by Steven Farmer.

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